Sodium hydride → 2-(5-difluoromethoxy-1-pyridin-3-ylmethyl-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid tert-butylamide

HRID 246306

반응식

HRID 246306 반응식
[C:1]([NH:5][C:6]([C:8]1[C:16]2[C:11](=[N:12][CH:13]=[C:14]([C:17]3[C:25]4[C:20](=[CH:21][CH:22]=[C:23]([O:26][CH:27]([F:29])[F:28])[CH:24]=4)[NH:19][N:18]=3)[N:15]=2)[N:10]([CH2:30][O:31][CH2:32][CH2:33][Si:34]([CH3:37])([CH3:36])[CH3:35])[CH:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].Br.Br[CH2:42][C:43]1[CH:44]=[N:45][CH:46]=[CH:47][CH:48]=1>CN(C=O)C>[C:1]([NH:5][C:6]([C:8]1[C:16]2[C:11](=[N:12][CH:13]=[C:14]([C:17]3[C:25]4[C:20](=[CH:21][CH:22]=[C:23]([O:26][CH:27]([F:28])[F:29])[CH:24]=4)[N:19]([CH2:42][C:43]4[CH:44]=[N:45][CH:46]=[CH:47][CH:48]=4)[N:18]=3)[N:15]=2)[N:10]([CH2:30][O:31][CH2:32][CH2:33][Si:34]([CH3:37])([CH3:36])[CH3:35])[CH:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 127070373-(Bromomethyl)pyridine hydrobromideHCID 712795662-(5-difluoromethoxy-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid tert-butylamide

생성물 1

HCID 712807112-(5-difluoromethoxy-1-pyridin-3-ylmethyl-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid tert-butylamide수율 90%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
0 °C

실험 절차

In a 25 ml round-bottomed flask, 2-(5-difluoromethoxy-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid tert-butylamide (120 mg, 0.23 mmol) was dissolved in DMF (1.7 ml). The light yellow solution was cooled to 0° C. and sodium hydride (60% in mineral oil, 37 mg, 0.93 mmol) was added. The reaction was stirred at 0° C. for 15 min then 3-(bromomethyl)pyridine hydrobromide (91 mg, 0.36 mmol) was added. The reaction mixture was stirred at 0° C. for 1 h then quenched with water and diluted with petroleum ether. The suspension was filtered, washed with water and petroleum ether and the product collected was dried under high vacuum to afford 126 mg (90%) of 2-(5-difluoromethoxy-1-pyridin-3-ylmethyl-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid tert-butylamide as a yellow powder.

후처리

  1. stirringThe reaction mixture was stirred at 0° C. for 1 h
  2. customthen quenched with water
  3. additiondiluted with petroleum ether
  4. filtrationThe suspension was filtered
  5. washwashed with water and petroleum ether
  6. customthe product collected
  7. customwas dried under high vacuum

출처 및 근거

ORD 기록
ord-2f62d447a62141799ffeb7339ac01f45
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08658646B2

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