Water → 2-(6-fluoro-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanylethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid ((R)-2,2-difluoro-1-methyl-propyl)-amide

HRID 245911

반응식

HRID 245911 반응식
C(N(CC)C(C)C)(C)C.[F:10][C:11]1[CH:19]=[C:18]2[C:14]([C:15]([C:21]3[N:22]=[C:23]4[C:29]([C:30](O)=[O:31])=[CH:28][N:27]([CH2:33][O:34][CH2:35][CH2:36][Si:37]([CH3:40])([CH3:39])[CH3:38])[C:24]4=[N:25][CH:26]=3)=[N:16][N:17]2[CH3:20])=[CH:13][CH:12]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.O.FC(F)(F)C(O)=O.[F:73][C:74]([F:79])([CH3:78])[C@H:75]([NH2:77])[CH3:76]>CN(C=O)C>[F:73][C:74]([F:79])([CH3:78])[C@H:75]([NH:77][C:30]([C:29]1[C:23]2[C:24](=[N:25][CH:26]=[C:21]([C:15]3[C:14]4[C:18](=[CH:19][C:11]([F:10])=[CH:12][CH:13]=4)[N:17]([CH3:20])[N:16]=3)[N:22]=2)[N:27]([CH2:33][O:34][CH2:35][CH2:36][Si:37]([CH3:40])([CH3:39])[CH3:38])[CH:28]=1)=[O:31])[CH3:76]

참가 물질

7

반응물 5

HCID 962WaterHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 712796202-(6-fluoro-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acidHCID 86677918(R)-2,2-difluoro-1-methyl-propylamine trifluoroacetate

생성물 1

HCID 712860802-(6-fluoro-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanylethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid ((R)-2,2-difluoro-1-methyl-propyl)-amide수율 81%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

In a round-bottomed flask, (R)-2,2-difluoro-1-methyl-propylamine trifluoroacetate (crude from Step 4) was dissolved in DMF (1.2 ml) and N,N-diisopropylethylamine (0.5 ml, 2.86 mmol) was added. Then 2-(6-fluoro-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (110 mg, 0.25 mmol) was added followed by HATU (104 mg, 0.27 mmol). The yellow solution was stirred at room temperature overnight. Water was added and the suspension was filtered. The filter cake was washed with water and petroleum ether then dried under high vacuum to afford 108 mg (81%) of 2-(6-fluoro-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid ((R)-2,2-difluoro-1-methyl-propyl)-amide as an off-white powder.

후처리

  1. filtrationthe suspension was filtered
  2. washThe filter cake was washed with water and petroleum ether
  3. customthen dried under high vacuum

출처 및 근거

ORD 기록
ord-0132097983cb4364a87047221a3419ad
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08658646B2

연결된 노트

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