Sodium triacetoxyborohydride → 5-(5-{[[(3,5-dimethyl-1H-pyrazol-4-yl)methyl](methyl)amino]methyl}-3-thienyl)-3-[1-(ethylsulfonyl)-4-piperidinyl]-1H-indole-7-carboxamide

HRID 1806498노트

반응식

HRID 1806498 반응식
[CH2:1]([S:3]([N:6]1[CH2:11][CH2:10][CH:9]([C:12]2[C:20]3[C:15](=[C:16]([C:28]([NH2:30])=[O:29])[CH:17]=[C:18]([C:21]4[CH:25]=[C:24]([CH:26]=O)[S:23][CH:22]=4)[CH:19]=3)[NH:14][CH:13]=2)[CH2:8][CH2:7]1)(=[O:5])=[O:4])[CH3:2].[CH3:31][C:32]1[C:36]([CH2:37][NH:38][CH3:39])=[C:35]([CH3:40])[NH:34][N:33]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CS(C)=O.C(O)(=O)C>[CH3:31][C:32]1[C:36]([CH2:37][N:38]([CH2:26][C:24]2[S:23][CH:22]=[C:21]([C:18]3[CH:19]=[C:20]4[C:15](=[C:16]([C:28]([NH2:30])=[O:29])[CH:17]=3)[NH:14][CH:13]=[C:12]4[CH:9]3[CH2:8][CH2:7][N:6]([S:3]([CH2:1][CH3:2])(=[O:5])=[O:4])[CH2:11][CH2:10]3)[CH:25]=2)[CH3:39])=[C:35]([CH3:40])[NH:34][N:33]=1

참가 물질

6

반응물 3

HCID 5049666Sodium triacetoxyborohydrideHCID 28305800HCID 28305800, 화합물HCID 577327033-[1-(ethylsulfonyl)-4-piperidinyl]-5-(5-formyl-3-thienyl)-1H-indole-7-carboxamide

생성물 1

HCID 577327235-(5-{[[(3,5-dimethyl-1H-pyrazol-4-yl)methyl](methyl)amino]methyl}-3-thienyl)-3-[1-(ethylsulfonyl)-4-piperidinyl]-1H-indole-7-carboxamide수율 11%

시약·촉매·용매 2

HCID 176Acetic Acid촉매HCID 679Dimethyl Sulfoxide용매

실험 절차

To a solution of 3-[1-(ethylsulfonyl)-4-piperidinyl]-5-(5-formyl-3-thienyl)-1H-indole-7-carboxamide (45 mg, 100 μmol) in dimethyl sulfoxide (1.0 mL) was added 1-(3,5-dimethyl-1H-pyrazol-4-yl)-N-methylmethanamine (320 μmol) and 2 to 3 drops of glacial acetic acid. The resulting mixture is agitated overnight. After 18 h, sodium triacetoxyborohydride (200 mg, 1000 μmol) is added. This mixture is agitated for 1.5 h followed by purification by Gilson Preparatory HPLC to give 6.24 mg of the title compound (11.0%).

후처리

  1. waitAfter 18 h
  2. stirringThis mixture is agitated for 1.5 h
  3. customfollowed by purification by Gilson Preparatory HPLC

출처 및 근거

ORD 기록
ord-fb08dfbc1456412cbd00d3ef7d3d03d9
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08354406B2

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