HRID52029

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID10340

Carbonic acid sodium salt (1:2)

CNa2O3

HCID81079

2-Chloronicotinonitrile

C6H3ClN2

结构：CO[C@@H]1CN(CCCCN)CC[C@@H]1NC(=O)c1cc(Cl)c(N)c2c1OCC2

HCID67704528

未命名化合物

PRODUCTS

生成物

结构：CO[C@@H]1CN(CCCCNc2ncccc2C#N)CC[C@@H]1NC(=O)c1cc(Cl)c(N)c2c1OCC2.CO[C@@H]1CN(CCCCNc2ncccc2C#N)CC[C@@H]1NC(=O)c1cc(Cl)c(N)c2c1OCC2.O

HCID131718800

未命名化合物

收率 35.4%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID6228

N,N-Dimethylformamide

C3H7NO

CONDITIONS

反应条件

温度: 70 °C

PROCEDURE

实验过程

A mixture of 1.4 parts of 2-chloro-3-pyridinecarbonitrile, 3.2 parts of cis-4-amino-N-[1-(4-aminobutyl)-3-methoxy -4-piperidinyl]-5-chloro-2,3-dihydro-7-benzofurancarboxamide, 65.8 parts of N,N-dimethylformamide and 1.3 parts of sodium carbonate was stirred for 20 hours at 70° C. The solvent was evaporated and the residue was dissolved in trichloromethane. The organic layer was washed with water, dried, filtered and evaporated. The residue was purified by column chromatography (silica gel; CHCl3 /CH3OH(NH3)98:2). The eluent of the desired fraction was evaporated and the residue was crystallized from 2,2'-oxybispropane. The product was dried in vacuo at 60° C., yielding 1.44 parts (35.4%) of cis-4-amino-5-chloro-N-[1-[4-[(3-cyano-2-pyridinyl)-amino]butyl]-3-methoxy-4-piperidinyl]-2,3-dihydro-7-benzofurancarboxamide hemihydrate; mp. 129.7° C. (comp. 6).

WORKUP

后处理

customThe solvent was evaporated
dissolutionthe residue was dissolved in trichloromethane
washThe organic layer was washed with water
customdried
filtrationfiltered
customevaporated
customThe residue was purified by column chromatography (silica gel; CHCl3 /CH3OH(NH3)98:2)
customThe eluent of the desired fraction was evaporated
customthe residue was crystallized from 2,2'-oxybispropane
customThe product was dried in vacuo at 60° C.

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-845bc1ef200f4d7098c763399ef04796
来源数据集: uspto-grants-1997_04
DOI: 10.6084/m9.figshare.5104873.v1
专利: US05616583
来源说明: uspto-grants-1997_04

反应 SMILES

Cl[C:2]1[C:7]([C:8]#[N:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[NH2:10][C:11]1[C:16]2[CH2:17][CH2:18][O:19][C:15]=2[C:14]([C:20]([NH:22][C@H:23]2[CH2:28][CH2:27][N:26]([CH2:29][CH2:30][CH2:31][CH2:32][NH2:33])[CH2:25][C@H:24]2[O:34][CH3:35])=[O:21])=[CH:13][C:12]=1[Cl:36].C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O>[OH2:19].[NH2:10][C:11]1[C:16]2[CH2:17][CH2:18][O:19][C:15]=2[C:14]([C:20]([NH:22][C@H:23]2[CH2:28][CH2:27][N:26]([CH2:29][CH2:30][CH2:31][CH2:32][NH:33][C:2]3[C:7]([C:8]#[N:9])=[CH:6][CH:5]=[CH:4][N:3]=3)[CH2:25][C@H:24]2[O:34][CH3:35])=[O:21])=[CH:13][C:12]=1[Cl:36].[NH2:10][C:11]1[C:16]2[CH2:17][CH2:18][O:19][C:15]=2[C:14]([C:20]([NH:22][C@H:23]2[CH2:28][CH2:27][N:26]([CH2:29][CH2:30][CH2:31][CH2:32][NH:33][C:2]3[C:7]([C:8]#[N:9])=[CH:6][CH:5]=[CH:4][N:3]=3)[CH2:25][C@H:24]2[O:34][CH3:35])=[O:21])=[CH:13][C:12]=1[Cl:36]