HRID245732

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)c1cc2ccsc2n1C

HCID67364476

未命名化合物

结构：Cc1nccn2c1c(Br)nc2[C@H]1CC[C@H](N2CCN(C)CC2)CC1

HCID178432912

未命名化合物

PRODUCTS

生成物

结构：COc1cc(-c2nc([C@H]3CC[C@H](N4CCN(C)CC4)CC3)n3ccnc(C)c23)ccc1NC(=O)c1cc2ccsc2n1C

HCID178487942

未命名化合物

收率 28.4%

PROCEDURE

实验过程

Reaction of N-(2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-6-methyl-6H-thieno[2,3-b]pyrrole-5-carboxamide (32 mg) and 1-bromo-8-methyl-3-((trans)-4-(4-methylpiperazin-1-yl)cyclohexyl)imidazo[1,5-a]pyrazine (30 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) gave N-(2-methoxy-4-(8-methyl-3-((trans)-4-(4-methylpiperazin-1-yl)cyclohexyl)imidazo[1,5-a]pyrazin-1-yl)phenyl)-6-methyl-6H-thieno[2,3-b]pyrrole-5-carboxamide (13 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)

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-6e97c52d86d748feae76aff460e3b1bc
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

[CH3:1][O:2][C:3]1[CH:8]=[C:7](B2OC(C)(C)C(C)(C)O2)[CH:6]=[CH:5][C:4]=1[NH:18][C:19]([C:21]1[N:25]([CH3:26])[C:24]2[S:27][CH:28]=[CH:29][C:23]=2[CH:22]=1)=[O:20].Br[C:31]1[N:32]=[C:33]([C@H:41]2[CH2:46][CH2:45][C@H:44]([N:47]3[CH2:52][CH2:51][N:50]([CH3:53])[CH2:49][CH2:48]3)[CH2:43][CH2:42]2)[N:34]2[CH:39]=[CH:38][N:37]=[C:36]([CH3:40])[C:35]=12>>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([C:31]2[N:32]=[C:33]([C@H:41]3[CH2:42][CH2:43][C@H:44]([N:47]4[CH2:48][CH2:49][N:50]([CH3:53])[CH2:51][CH2:52]4)[CH2:45][CH2:46]3)[N:34]3[CH:39]=[CH:38][N:37]=[C:36]([CH3:40])[C:35]=23)[CH:6]=[CH:5][C:4]=1[NH:18][C:19]([C:21]1[N:25]([CH3:26])[C:24]2[S:27][CH:28]=[CH:29][C:23]=2[CH:22]=1)=[O:20]