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

HRID 2067291Notes

Reaction equation

HRID 2067291 reaction equation
[N:1]([C:4]1[CH:5]=[CH:6][C:7]([CH3:27])=[C:8]([C:10]([C:12]2[CH:17]=[CH:16][C:15]([NH:18][C:19]3[CH:20]=[C:21]([CH3:25])[CH:22]=[CH:23][CH:24]=3)=[CH:14][C:13]=2[Cl:26])=[O:11])[CH:9]=1)=[N+:2]=[N-:3].[CH2:28]([OH:32])[CH2:29][C:30]#[CH:31]>>[Cl:26][C:13]1[CH:14]=[C:15]([NH:18][C:19]2[CH:20]=[C:21]([CH3:25])[CH:22]=[CH:23][CH:24]=2)[CH:16]=[CH:17][C:12]=1[C:10]([C:8]1[CH:9]=[C:4]([N:1]2[CH:31]=[C:30]([CH2:29][CH2:28][OH:32])[N:3]=[N:2]2)[CH:5]=[CH:6][C:7]=1[CH3:27])=[O:11]

Participants

3

Reactant 2

HCID 135663-Butyn-1-OLHCID 86605540(5-Azido-2-methyl-phenyl)-(2-chloro-4-m-tolylamino-phenyl)-methanone

Product 1

HCID 11539606(2-Chloro-4-m-tolylamino-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 465 (0.25 mmol) and but-3-yn-1-ol (0.30 mmol). The crude product was purified by flash chromatography using EtOAc/petroleum ether (40-60) 6:1 as the eluent to afford the title compound as light yellow foam. 13C NMR (CDCl3) δ 194.8, 148.9, 146.3, 141.1, 139.7, 139.6, 138.1, 135.6, 134.8, 134.0, 132.5, 129.5, 127.5, 125.2, 122.3, 122.2, 120.7, 119.9, 118.7, 116.3, 112.8, 61.6, 28.7, 21.5, 19.9

Workup

  1. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-fee3e325407844be9add7e3311a5ac24
Source dataset
uspto-grants-2012_10
Patent number
US08293772B2

Reaction notes

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