Category: 937046-98-5

Synthetic Route of 937046-98-5, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 937046-98-5, name is 7-Bromopyrrolo[2,1-f][1,2,4]triazin-4-amine belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

f. Preparation of Compound 407. To a dry, argon purged round bottom flask (100 mL) were added 7-bromo-pyrrolo[2, 1 – f][1 ,2,4]triazin-4-ylamine (234 mg, 1.10 mmol) (prepared according to WO2007056170) and anhydrous THF (1.5 mL). TMSCI (276 iL, 2.2 mmol) was then added and the reaction mixture stirred for 2 hours. The flask was placed into a dry ice/acetone bath (-78 C) and BuLi (2.5 mL, 4.0 mmol, 1.6M in hexanes) was added dropwise. After 1 hour, a solution of compound 406 (432.5 mg, 1.0 mmol) in THF was cooled to 0 C and then added to the reaction flask dropwise. After 1 hour of stirring at -78 C, the flask was warmed to 0 C and sat. NH4CI (5 mL) was added to quench the reaction. The organics were extracted using EtOAc (3 x 10 mL) and the combined organic layers were dried using MgS0 . The solvent was removed under reduced pressure and the crude material was purified using flash chromatography (hexanes / EtOAc). 560 mg (90 %) of compound 407 was isolated as a mixture of two anomers. LC/MS = 567.2 (M + H+). H NMR (300 MHz, CDCI3): delta 7.85 (m, 1 H), 7.27 (m, 15H), 7.01 (m, 1 H), 6.51 (m, 1 H), 4.66 (m, 8H), 4.40 (m, 2H), 3.79 (m, 3H), 1.62 (s, 2′-CH3 from the one anomer), 1.18 (s, 2′-CH3 from the other anomer).

The synthetic route of 7-Bromopyrrolo[2,1-f][1,2,4]triazin-4-amine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GILEAD SCIENCES, INC.; RAY, Adrian S.; WATKINS, William J.; LINK, John O.; OLDACH, David W.; DELANEY, IV, William E.; WO2013/40492; (2013); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 937046-98-5, name is 7-Bromopyrrolo[2,1-f][1,2,4]triazin-4-amine belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. COA of Formula: C6H5BrN4

To a solution of Intermediate B (195 mg, 0.91 mmol) in THF at -78 0C under N2 was added dropwise n-butyllithium (1.46 ml, 3.66 mmol). The reaction mixture was stirred for 15 min and then gaseous ethylene oxide was bubbled into the reaction mixture for 5 min. The diy-ice bath was removed and warmed up to rt. Analytical HPLC found a new peak and then the reaction was quenched with 2 ml saturated aq NH4Cl followed by addition of 10 ml EtOAc and H2O (2ml). The organic phase was collected and washed with brine and dried over Na2SO4 and evaporated to crude as yellow oil. The crude was dissolved in 5 ml 10%MeOH/CH2Cl2 and 4 ml silica gel was added and then solvent evaporated. The crude in the silica gel was loaded on an MPLC column and was eluted with a gradient 0 – 10%MeOH in CH2Cl2 to give 20 mg of the desired product. ; MS [M+H]+ = 178.9; LCMS RT = 1.1 min

The synthetic route of 937046-98-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER PHARMACEUTICALS CORPORATION; WO2007/64931; (2007); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 937046-98-5,Some common heterocyclic compound, 937046-98-5, name is 7-Bromopyrrolo[2,1-f][1,2,4]triazin-4-amine, molecular formula is C6H5BrN4, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

To a degassed solution of 7-bromopyrrolo[2,l-f][l,2,4]triazin-4-ylamine (10.0 g, 46.9 mmol) in anhydrous DMF (78 mL) and triethylamine (47 mL) was added tetrakis(triphenylphosphine)palladium(0) (2.17 g, 1.88 mmol, 0.04 eq) and copper (I) bromide dimethylsulfide complex (0.77 g, 3.75 mmol, 0.08 eq). After degassing with N2 for 5 min., propargyl alcohol (8.2 mL, 140.8 mmol, 3.0 eq) was added, and the reaction mixture was stirred at 900C for 6h. The reaction was quenched with 5% aq. NH3 in saturated aq. NH4Cl. The aqeuous layer was washed with EtOAc (Ix) followed by 25% iPrOH in DCM (3x). The combined organic layers were dried over MgSO4, filtered through a pad of celite, and concentrated at reduced pressure. The crude product was purified by MPLC eluted with 5% EtOH/DCM. Trituration from EtOAc afforded 4.75 g (53.8%) of the desired product as a yellow solid. 1H-NMR (DMSO-^6) §7.89 (s, IH), 7.88 (broad s, 2H), 6.85 (dd, 2H), 5.39 (t, IH), 4.36 (d, 2H); MS LC-MS [M+H]+ = 189, RT = 1.08 min.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 7-Bromopyrrolo[2,1-f][1,2,4]triazin-4-amine, its application will become more common.

Reference:
Patent; BAYER PHARMACEUTICALS CORPORATION; WO2007/64931; (2007); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 937046-98-5, name is 7-Bromopyrrolo[2,1-f][1,2,4]triazin-4-amine, A new synthetic method of this compound is introduced below., Recommanded Product: 937046-98-5

To a dry, argon purged round bottom flask (100 mL) were added 7-bromo- pyrrolo[2,l-f][1,2,4]triazin-4-ylamine (234 mg, 1.10 mmol) and anhydrous THF (1 .5 mL). TMSCI (276 L, 2.2 mmol) was then added and the reaction mixture stirred for 2h. The flask was placed into a dry ice/acetone bath (- 78 C) and BuLi (2.5 mL, 4.0 mmol, 1.6 M in hexanes) was added dropwise. After 1 h, a solution of 2b (432 mg, 1.0 mmol) in THF was cooled to 0 C and then added to the reaction flask dropwise. After 1 h of stirring at -78 C, the flask was warmed to 0 C and sat. NH4CI (5 mL) was added to quench the reaction. The organics were extracted using EtOAc (3 10 mL) and the combined organic layers were dried using MgS04. The solvent was removed under reduced pressure and the crude material was purified using flash silica gel chromatography (hexanes / EtOAc). 560 mg (90 %) of the desired material 2c was isolated. LC/MS = 567.2 (M + H+). 1H NMR (300 MHz, CDC13): 5 7.85 (m, 1H), 7.27 (m, 15H), 7.01 (m, 1H), 6.51 (m, 1H), 4.66 (m, 8H), 4.40 (m, 2H), 3.79 (m, 3H), 1.62 (s,.2′-CH3 from the one anomer), 1.18 (s, 2′-CH3 from the other anomer).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; GILEAD SCIENCES, INC.; BUTLER, Thomas; CHO, Aesop; GRAETZ, Benjamin, R.; KIM, Choung, U.; METOBO, Samuel, E.; SAUNDERS, Oliver, L.; WALTMAN, Andrew, W.; XU, Jie; ZHANG, Lijun; WO2011/35250; (2011); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 937046-98-5, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 937046-98-5, name is 7-Bromopyrrolo[2,1-f][1,2,4]triazin-4-amine belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A mixture of 7-bromopyrrolo[2,1-f][1,2,4]triazin- 4-amine (250 mg, 1.174 mmol), (S)-1-tert-butyl 2-methyl 4-(4,4,5,5-tetramethyl-1,3,2- dioxaborolan-2-yl)-1H-pyrrole-1,2(2H,5H)-dicarboxylate (912 mg, 2.58 mmol) and potassium phosphate tribasic (2 M in water) (1760 mul, 3.52 mmol) in DMF (6593 mul) was sparged with nitrogen for 5 min. PdCl2(dppf)-CH2Cl2 adduct (96 mg, 0.117 mmol) was added to the reaction mixture which was sparged with nitrogen for an additional 5 min. The mixture was brought to 100 C and stirred for 30 min. The reaction mixture was then diluted with EtOAc, washed with water, brine, dried over MgSO4, filtered and concentrated in vacuo. Purification by flash chromatography (Silica, 40g, 40 – 70% EtOAc/Hexanes) gave (S)-1-tert-butyl 2-methyl 4-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7- yl)-1H-pyrrole-1,2(2H,5H)-dicarboxylate (165 mg, 0.459 mmol, 39.1 % yield). (0757) MS ESI (m/z) 360.1 (M+H)

The synthetic route of 7-Bromopyrrolo[2,1-f][1,2,4]triazin-4-amine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WATTERSON, Scott Hunter; ANDAPPAN MURUGAIAH SUBBAIAH, Murugaiah; DZIERBA, Carolyn Diane; GONG, Hua; GUERNON, Jason M.; GUO, Junqing; HART, Amy C.; LUO, Guanglin; MACOR, John E.; PITTS, William J.; SHI, Jianliang; VENABLES, Brian Lee; WEIGELT, Carolyn A.; WU, Yong-Jin; ZHENG, Zhizhen Barbara; SIT, Sing-Yuen; CHEN, Jie; (810 pag.)WO2019/147782; (2019); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 937046-98-5,Some common heterocyclic compound, 937046-98-5, name is 7-Bromopyrrolo[2,1-f][1,2,4]triazin-4-amine, molecular formula is C6H5BrN4, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Into a 250-mL round-bottom flask purged and maintained with an inert atmosphere of argon, was placed a solution of compound 2a (3.2 g, 15.02 mmol) in THF (40 mL). n-Butyllithium (18.75 mL, 1.6 N in THF) was added dropwise at -78C, and then chloro[2-(chlorodimethylsilyl)ethyl]dimethylsilane (3.2 g, 14.87 mmol) was added at -78 C. After the resulting solution was stirred for 0.5 hours at -78 C, n- butyllithium (6.25 mL, 1.6 N in THF) was added. After the resulting mixture was stirred for 5 minutes, a solution of compound lh (3.7 g, 9.75 mmol) in THF (10 mL) was added to the mixture and the resulting solution was stirred for 2 hours at -78C. After that the reaction was quenched by the addition of 30 mL saturated aqueous solution of ammonium chloride, extracted with ethyl acetate (3×150 mL), dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was applied onto a silica gel column and eluted with ethyl acetate/petroleum ether (1 :20~1 :3) to provide 350 mg (7%) of compound 2c as an off-white solid. LC-MS: (ES, m/z): 514.0 [M+H]+

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 7-Bromopyrrolo[2,1-f][1,2,4]triazin-4-amine, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; GIRIJAVALLABHAN, Vinay; BOGEN, Stephane; PAN, Weidong; DANG, Qun; DAVIES, Ian; WO2014/59901; (2014); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 937046-98-5, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 937046-98-5, name is 7-Bromopyrrolo[2,1-f][1,2,4]triazin-4-amine, This compound has unique chemical properties. The synthetic route is as follows.

To a suspension of N-methyltetrahydro-2H-pyran-4-amine (541 mg, 4.69 mmol) and (3-(bromomethyl)phenyl)boronic acid (756 mg, 3.52 mmol) in acetonitrile (8 mL) was added K2C03 (973 mg, 7.04 mmol) under anhydrous conditions. After stirring at room temperature for 10 h, the reaction mixture was concentrated, phosphoric acid,potassium salt (1.50 g, 2.35 mmol), 7-bromopyrrolo[2,1-f][1,2,4]triazin-4-amine (500 mg, 2.347 mmol), dioxane (8 mL) and water (4 mL) were added. The reaction vessel was evacuated, backfilled with N2 and then degassed by bubbling N2 with sonication. Tetrakis triphenylphosphine (271 mg, 0.235 mol) was added and the degassing process was repeated. The resulting reaction mixture was heated at 140 C in a microwave for 45mm. The reaction complex was cooled, filtered, and washed with water. The filtrate was extracted with ethyl acetate (10 mL x 3). The organic layers were combined, dried and concentrated. The crude mixture was dissolved in DMF, and purified by preparative LC Method C to obtain 7-(3 -((methyl(tetrahydro-2H-pyran-4-yl)amino)methyl)phenyl) pyrrolo[2,1-f][1,2,4]triazin-4-amine, TFA (636 mg, 60% yield). LC/MS (M+H) =338.30.

The chemical industry reduces the impact on the environment during synthesis 7-Bromopyrrolo[2,1-f][1,2,4]triazin-4-amine. I believe this compound will play a more active role in future production and life.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; BHIDE, Rajeev S.; BATT, Douglas G.; CHERNEY, Robert J.; CORNELIUS, Lyndon A.M.; LIU, Qingjie; MARCOUX, David; NEELS, James; POSS, Michael A.; QIN, Lan-ying; RUAN, Zheming; SHI, Qing; SRIVASTAVA, Anurag S.; TINO, Joseph A.; WATTERSON, Scott Hunter; (532 pag.)WO2016/64957; (2016); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 937046-98-5, name is 7-Bromopyrrolo[2,1-f][1,2,4]triazin-4-amine, A new synthetic method of this compound is introduced below., SDS of cas: 937046-98-5

Example 28: tert-butyl 3-(4-aminopyrrolo[2,l-fj[l,2,4]triazin-7-yl)-3-hydroxypiperidine-l-carboxylateTo a stirred suspension of 7-bromopyrrolo[2,l-fJ[l,2,4]triazin-4-amine (3.0 g, 14 mmol) in tetrahydrofuran (75 mL) was added chlorotrimethylsilane (4.5 mL, 35 mmol) dropwise. The reaction mixture was stirred at room temperature for 3 hours and a 2M solution of 2- propylmagnesium chloride in THF (37 mL, 74 mmol) was added dropwise. After 3 hours, tert-butyl 3-oxopiperidine-l-carboxylate (5.6 g, 28 mmol) was added in one portion. The mixture was stirred at room temperature overnight at which time LC/MS indicated the reaction was complete. The reaction was poured over a mixture of ice and saturated aqueous ammonium chloride (500 mL). The mixture was allowed to warm to room temperature and was extracted with ethyl acetate (250 mL) four times. The combined organic layers were washed with saturated brine, dried over sodium sulfate and concentrated under reduced pressure. The crude solid was triturated with a 2:1 mixture of ethyl acetate:heptane to obtain the title compound (2g) having the following physical data.1HNMR (300 MHz, DMSO) delta 7.84 (s, IH), 7.71 (bs, 2H), 6.83 (d, J = 4, IH) 6.60 (d, J = 4, IH), 5.17 (s, IH), 3.94 – 3.76 (m, IH), 3.71 – 3.44 (m, 2H), 3.18 – 2.99 (m, IH), 2.52 – 2.42 (m, 2H), 1.99 – 1.74 (m, 2H), 1.46 – 1.09 (m, 9H); (LCMS) M+= 334.2, RT = 4.67min.

The synthetic route of 937046-98-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LOCUS PHARMACEUTICALS, INC.; KONTEATIS, Zenon; MOFFETT, Kristofer; LEE, Younghee; CHAO, Wenchun; WONG, Dora Do-York; WO2010/126960; (2010); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 937046-98-5,Some common heterocyclic compound, 937046-98-5, name is 7-Bromopyrrolo[2,1-f][1,2,4]triazin-4-amine, molecular formula is C6H5BrN4, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

The bromopyrazole (prepared according to WO2009/132135) (0.5 g, 2.4 mmol) was suspended in anhydrous THF (10 mL) under N2(g). The suspension was stirred and TMSC1 (0.67 mL, 5.28 mmol) was added. The mixture was stirred for 20 min. at RT and then cooled to -78 C after which time a solution of n-BuLi (6 mL, 1.6 N in hexanes, 9.6 mmol) was added slowly. The reaction mixture was stirred for 10 min. at -78 C and then the lactone (1 g, 2.4 mmol) was added via syringe. When the reaction was complete as measured by LCMS, AcOH was added to quench the reaction. The mixture was concentrated under reduced pressure and the residue dissolved in a mixture of CH2C12 and H20 (100 mL, 1 :1). The organic layer was separated and washed with H20 (50 mL). The organic layer was then dried over anhydrous MgSC>4, filtered and concentrated under reduced pressure. The residue was subjected to silica gel chromatography eluting with0-50% EtOAc in hexanes to provide the product as a 1 :1 mixture of anomers (345 mg, 26% yield).LCMS m/z 553 [M+H].

The synthetic route of 937046-98-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GILEAD SCIENCES, INC.; MACKMAN, Richard, L.; PARRISH, Jay, P.; RAY, Adrian, S.; THEODORE, Dorothy, Agnes; WO2012/12776; (2012); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 937046-98-5, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 937046-98-5, name is 7-Bromopyrrolo[2,1-f][1,2,4]triazin-4-amine belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a stirred suspension of 7-bromopyrrolo[2,1-f][1,2,4]triazin-4-ylamine (0.372 g, 1.745 mmol) in THF (8mL) was added TMS-Cl (0.446 ml, 3.49 mmol) and the mixture was stirred at room temperature for 2 hours. The reaction was then cooled to -78 C. and n-BuLi (2.79 ml, 6.98 mmol) was added dropwise. The mixture was stirred at -78 C. for 1 hour and then Int 21h (0.69 g, 1.745 mmol) dissolved in THF (2 mL) was added dropwise. After 10 min at -78 C., the reaction mixture was allowed to warm up to 0 C. over 40 minutes. The reaction was quenched with aqueous ammonium chloride (15 mL) and then extracted with ethyl acetate (3×30 mL). The combined organic layers were dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography using a gradient of 10-70% EtOAc in hexane to provide Int 21i as a mixture of isomers (240 mg).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 7-Bromopyrrolo[2,1-f][1,2,4]triazin-4-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Merck Sharp & Dohme Corp.; Girijavallabhan, Vinay; Njoroge, F. George; Bogen, Stephane; Bennett, Frank; Verma, Vishal; Arasappan, Ashok; Chen, Kevin X.; Huang, Ying; Kerekes, Angela; Nair, Latha; Pissarnitski, Dimitri; Dang, Qun; Davies, Ian; Olsen, David B.; Stamford, Andrew; Vacca, Joseph P.; US2014/206640; (2014); A1;,
Bromide – Wikipedia,
bromide – Wiktionary