HRID1806498

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID5049666

Sodium triacetoxyborohydride

C6H10BNaO6

HCID28305800

未命名化合物

结构：CCS(=O)(=O)N1CCC(c2c[nH]c3c(C(N)=O)cc(-c4csc(C=O)c4)cc23)CC1

HCID57732703

未命名化合物

PRODUCTS

生成物

结构：CCS(=O)(=O)N1CCC(c2c[nH]c3c(C(N)=O)cc(-c4csc(CN(C)Cc5c(C)n[nH]c5C)c4)cc23)CC1

HCID57732723

未命名化合物

收率 11%

AUXILIARIES

试剂、催化剂与溶剂

催化剂HCID176

Acetic Acid

C2H4O2

溶剂HCID679

Dimethyl sulfoxide

C2H6OS

PROCEDURE

实验过程

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%).

WORKUP

后处理

waitAfter 18 h
stirringThis mixture is agitated for 1.5 h
customfollowed by purification by Gilson Preparatory HPLC

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-fb08dfbc1456412cbd00d3ef7d3d03d9
来源数据集: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
专利: US08354406B2
来源说明: uspto-grants-2013_01

反应 SMILES

[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