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

HRID 2067235Notes

Reaction equation

HRID 2067235 reaction equation
C(OC(=O)CN1C=C([C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[C:13]([C:18](=[O:35])[C:19]3[CH:24]=[CH:23][C:22]([NH:25][C:26]4[CH:31]=[CH:30][C:29]([F:32])=[CH:28][C:27]=4[F:33])=[CH:21][C:20]=3[Cl:34])[CH:12]=2)N=N1)C.[N:37]([C:40]1C=CC(C)=[C:44]([C:46](C2C=CC(NC3C=CC(F)=CC=3F)=CC=2Cl)=[O:47])[CH:45]=1)=[N+:38]=[N-:39].C(O)CC#C>>[Cl:34][C:20]1[CH:21]=[C:22]([NH:25][C:26]2[CH:31]=[CH:30][C:29]([F:32])=[CH:28][C:27]=2[F:33])[CH:23]=[CH:24][C:19]=1[C:18]([C:13]1[CH:12]=[C:11]([N:37]2[CH:40]=[C:45]([CH2:44][CH2:46][OH:47])[N:39]=[N:38]2)[CH:16]=[CH:15][C:14]=1[CH3:17])=[O:35]

Participants

4

Reactant 3

HCID 135663-Butyn-1-OLHCID 11519102(4-{3-[2-Chloro-4-(2,4-difluoro-phenylamino)-benzoyl]-4-methyl-phenyl}-[1,2,3]triazol-1-yl)-acetic acid ethyl esterHCID 86605529(5-Azido-2-methyl-phenyl)-[2-chloro-4-(2,4-difluoro-phenylamino)-phenyl]-methanone

Product 1

HCID 11712482[2-Chloro-4-(2,4-difluoro-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 110, using compound 434 (6.87 mmol) and 3-butyne-1-ol (8.24 mmol). The crude product was purified by continuous gradient flash chromatography using EtOAc/petroleum ether (40-60) 50:50 to 100:0 as the eluent to afford the title compound as yellow foam.

Workup

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

Sources & evidence

ORD record
ord-caf9acdc6dc74d7291b826e9cb033f38
Source dataset
uspto-grants-2012_10
Patent number
US08293772B2

Reaction notes

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