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

HRID 246123
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HRID 246123 반응식
[CH3:1][C@@H:2]([NH:9][C:10]([C:12]1[C:20]2[C:15](=[N:16][CH:17]=[C:18]([C:21]3[C:29]4[C:24](=[CH:25][C:26]([F:30])=[CH:27][CH:28]=4)[N:23]([CH3:31])[N:22]=3)[N:19]=2)[N:14](COCC[Si](C)(C)C)[CH:13]=1)=[O:11])[CH2:3][N:4]1[CH:8]=[CH:7][CH:6]=[N:5]1.FC(F)(F)C(O)=O.C(N)CN.O>ClCCl.C(OCC)(=O)C>[CH3:1][C@@H:2]([NH:9][C:10]([C:12]1[C:20]2[C:15](=[N:16][CH:17]=[C:18]([C:21]3[C:29]4[C:24](=[CH:25][C:26]([F:30])=[CH:27][CH:28]=4)[N:23]([CH3:31])[N:22]=3)[N:19]=2)[NH:14][CH:13]=1)=[O:11])[CH2:3][N:4]1[CH:8]=[CH:7][CH:6]=[N:5]1
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참가 물질

7

반응물 4

HCID 962WaterHCID 3301EthylenediamineHCID 6422Trifluoroacetic acidHCID 712861932-(6-fluoro-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid ((R)-1-methyl-2-pyrazol-1-yl-ethyl)-amide

생성물 1

HCID 712859452-(6-fluoro-1-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid ((R)-1-methyl-2-pyrazol-1-yl-ethyl)-amide
수율 57%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

2-(6-Fluoro-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid ((R)-1-methyl-2-pyrazol-1-yl-ethyl)-amide (86 mg, 0.16 mmol) was dissolved in dichloromethane (2.2 ml) and cooled in ice bath. Trifluoroacetic acid (1 ml) was slowly added and the reaction was stirred at room temperature for 2 h. The reaction was evaporated and the residue was dissolved in dichloromethane (1 ml). Ethylenediamine (0.63 ml, 9.4 mmol) was added and the mixture was stirred for 18 h. Water and then ethyl acetate were added to the mixture. The resulting precipitate was filtered off, rinsed with water and diethyl ether and dried under high vacuum to give 37 mg (57%) of 2-(6-fluoro-1-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid ((R)-1-methyl-2-pyrazol-1-yl-ethyl)-amide. MS: (M+Na)+=441; mp=252-253° C. 1H NMR (300 MHz, DMSO-d6) δ: 9.08 (s, 1H), 8.46 (s, 1H), 8.21-8.33 (m, 1H), 8.12 (d, J=7.9 Hz, 1H), 7.63-7.75 (m, 2H), 7.31-7.40 (m, 1H), 6.97-7.10 (m, 1H), 6.12-6.23 (m, 1H), 4.46-4.63 (m, 1H), 4.32-4.44 (m, 2H), 4.14 (s, 3H), 1.23 (d, J=6.4 Hz, 3H).

후처리

  1. temperaturecooled in ice bath
  2. customThe reaction was evaporated
  3. dissolutionthe residue was dissolved in dichloromethane (1 ml)
  4. stirringthe mixture was stirred for 18 h
  5. filtrationThe resulting precipitate was filtered off
  6. washrinsed with water and diethyl ether
  7. customdried under high vacuum

출처 및 근거

ORD 기록
ord-fa037ef3f4a6423187a283e7b1ea594c
출처 데이터셋
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08658646B2

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