HRID245749

反应详情

EQUATION

反应方程式

REACTANTS

反应物

结构：COc1cc(B2OC(C)(C)C(C)(C)O2)ccc1NC(=O)c1cc2c(OC)cccc2n1C

HCID67365651

未命名化合物

结构：CNC[C@H]1CC[C@H](c2nc(Br)c3c(C)nccn32)CC1

HCID178484004

未命名化合物

PRODUCTS

生成物

结构：CNC[C@H]1CC[C@H](c2nc(-c3ccc(NC(=O)c4cc5c(OC)cccc5n4C)c(OC)c3)c3c(C)nccn32)CC1

HCID178484005

未命名化合物

收率 16.7%

PROCEDURE

实验过程

Reaction of the impure 1-((trans)-4-(1-bromo-8-methylimidazo[1,5-a]pyrazin-3-yl)cyclohexyl)-N-methylmethanamine (20 mg) and 4-methoxy-N-(2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1-methyl-1H-indole-2-carboxamide (26 mg) according to the procedure described in example 4 step 4c and purification by column chromatography (silica gel; dichloromethane with gradient 0 to 20% of methanol (containing 0.1% ammonium hydroxide)) gave 4-methoxy-N-(2-methoxy-4-(8-methyl-3-((trans)-4-((methylamino)methyl)cyclohexyl)imidazo[1,5-a]pyrazin-1-yl)phenyl)-1-methyl-1H-indole-2-carboxamide (5.6 mg)

WORKUP

后处理

customdescribed in example 4 step 4c and purification by column chromatography (silica gel; dichloromethane with gradient 0 to 20% of methanol (containing 0.1% ammonium hydroxide))

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-cc752875399a48d1919781db7c031c9e
来源数据集: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
专利: US08658794B2
来源说明: uspto-grants-2014_02

反应 SMILES

Br[C:2]1[N:3]=[C:4]([C@H:12]2[CH2:17][CH2:16][C@H:15]([CH2:18][NH:19][CH3:20])[CH2:14][CH2:13]2)[N:5]2[CH:10]=[CH:9][N:8]=[C:7]([CH3:11])[C:6]=12.[CH3:21][O:22][C:23]1[CH:31]=[CH:30][CH:29]=[C:28]2[C:24]=1[CH:25]=[C:26]([C:33]([NH:35][C:36]1[CH:41]=[CH:40][C:39](B3OC(C)(C)C(C)(C)O3)=[CH:38][C:37]=1[O:51][CH3:52])=[O:34])[N:27]2[CH3:32]>>[CH3:21][O:22][C:23]1[CH:31]=[CH:30][CH:29]=[C:28]2[C:24]=1[CH:25]=[C:26]([C:33]([NH:35][C:36]1[CH:41]=[CH:40][C:39]([C:2]3[N:3]=[C:4]([C@H:12]4[CH2:17][CH2:16][C@H:15]([CH2:18][NH:19][CH3:20])[CH2:14][CH2:13]4)[N:5]4[CH:10]=[CH:9][N:8]=[C:7]([CH3:11])[C:6]=34)=[CH:38][C:37]=1[O:51][CH3:52])=[O:34])[N:27]2[CH3:32]