Trifluoroacetic acid → N-tert-butyl-2-(5-(difluoromethoxy)-1-(3-hydroxybutyl)-1H-indazol-3-yl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide

HRID 246729ノート

反応式

HRID 246729 の反応式
[C:1]([NH:5][C:6]([C:8]1[C:12]2=[N: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)[N:19]([CH2:30][CH2:31][CH:32]([OH:34])[CH3:33])[N:18]=3)=[CH:15][N:16]=[C:11]2[N:10](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].FC(F)(F)C(O)=O>ClCCl>[C:1]([NH:5][C:6]([C:8]1[C:12]2=[N: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]([CH2:30][CH2:31][CH:32]([OH:34])[CH3:33])[N:18]=3)=[CH:15][N:16]=[C:11]2[NH:10][CH:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 71280582N-tert-butyl-2-(5-(difluoromethoxy)-1-(3-hydroxybutyl)-1H-indazol-3-yl)-5-trityl-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide

生成物 1

HCID 71280144N-tert-butyl-2-(5-(difluoromethoxy)-1-(3-hydroxybutyl)-1H-indazol-3-yl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide収率 30%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a stirred solution of N-tert-butyl-2-(5-(difluoromethoxy)-1-(3-hydroxybutyl)-1H-indazol-3-yl)-5-trityl-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide in dichloromethane (2 mL) was added drop-wise trifluoroacetic acid (1 mL) at room temperature. Then the reaction mixture was stirred for 1.5 hours. The solvent was removed under reduced pressure and the residue was purified by preparative-TLC (silica gel, petroleum ether:EtOAc=1:1) to give N-tert-butyl-2-(5-(difluoromethoxy)-1-(3-hydroxybutyl)-1H-indazol-3-yl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide (22 mg, 30% over three steps) as a white solid. MS: (M+H)+=473.2; 1H NMR (300 MHz, DMSO): δ 12.86 (s, 1H), 9.11 (s, 1H), 8.42 (s, 1H), 8.24 (d, 1H, J=1.8 Hz), 7.92-7.89 (m, 2H), 7.47-7.42 (m, 1H), 7.23 (t, 1H, J=74.4 Hz), 4.75-4.61 (m, 3H), 3.65 (brs, 1H), 2.06-1.92 (m, 2H), 1.53 (s, 9H), 1.15 (d, 3H, J=6.3 Hz).

後処理

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was purified by preparative-TLC (silica gel, petroleum ether:EtOAc=1:1)

出典と根拠

ORDレコード
ord-b29208c7b2114db5af668805112b4924
出典データセット
uspto-grants-2014_02
特許番号
US08658646B2

反応ノート

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