3-Butyn-1-OL → [2-Chloro-4-(2-methoxy-phenylamino)-phenyl]-{5-[4-(2-hydroxy-ethyl)-[1,2,3]triazol-1-yl]-2-methyl-phenyl}-methanone

HRID 2067256Notes

Reaction equation

HRID 2067256 reaction equation
[N:1]([C:4]1[CH:5]=[CH:6][C:7]([CH3:28])=[C:8]([C:10]([C:12]2[CH:17]=[CH:16][C:15]([NH:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[O:25][CH3:26])=[CH:14][C:13]=2[Cl:27])=[O:11])[CH:9]=1)=[N+:2]=[N-:3].[CH2:29]([OH:33])[CH2:30][C:31]#[CH:32]>>[Cl:27][C:13]1[CH:14]=[C:15]([NH:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[O:25][CH3:26])[CH:16]=[CH:17][C:12]=1[C:10]([C:8]1[CH:9]=[C:4]([N:1]2[CH:32]=[C:31]([CH2:30][CH2:29][OH:33])[N:3]=[N:2]2)[CH:5]=[CH:6][C:7]=1[CH3:28])=[O:11]

Participants

3

Reactant 2

HCID 135663-Butyn-1-OLHCID 86605532(5-Azido-2-methyl-phenyl)-[2-chloro-4-(2-methoxy-phenylamino)-phenyl]-methanone

Product 1

HCID 11503608[2-Chloro-4-(2-methoxy-phenylamino)-phenyl]-{5-[4-(2-hydroxy-ethyl)-[1,2,3]triazol-1-yl]-2-methyl-phenyl}-methanone

Procedure

The reaction was carried out similarly as described in the preparation of compound 116, using compound 442 (0.27 mmol) and but-3-yn-1-ol (0.30 mmol). The crude product was purified by continuous gradient flash chromatography using EtOAc/petroleum ether (40-60) 0:100 to 20:80 as the eluent to afford the title compound. 13C NMR (DMSO-d6) δ 193.6, 152.4, 150.2, 145.6, 141.1, 135.9, 134.4, 134.2, 134.0, 132.3, 128.2, 125.3, 124.6, 123.4, 121.0, 120.6, 118.8, 115.1, 112.2, 111.7, 60.1, 55.4, 29.1, 19.0

Workup

  1. customThe crude product was purified by continuous gradient flash chromatography

Sources & evidence

ORD record
ord-531460236f3145378a403edf0df36c67
Source dataset
uspto-grants-2012_10
Patent number
US08293772B2

Reaction notes

Loading…