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

HRID 2067234Notes

Reaction equation

HRID 2067234 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:10]=2F)[CH:5]=[CH:4][C:3]=1[C:17]([C:19]1[CH:24]=[C:23](C2N=NN(CCOC3CCCCO3)C=2)[CH:22]=[CH:21][C:20]=1[CH3:39])=[O:18].[N:40]([C:43]1C=CC(C)=[C:47]([C:49](C2C=CC(NC3C=CC(F)=CC=3)=CC=2Cl)=[O:50])[CH:48]=1)=[N+:41]=[N-:42].C(O)CC#C>>[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]2[CH:10]=[CH:11][C:12]([F:15])=[CH:13][CH:14]=2)[CH:5]=[CH:4][C:3]=1[C:17]([C:19]1[CH:24]=[C:23]([N:40]2[CH:43]=[C:48]([CH2:47][CH2:49][OH:50])[N:42]=[N:41]2)[CH:22]=[CH:21][C:20]=1[CH3:39])=[O:18]

Participants

4

Reactant 3

HCID 135663-Butyn-1-OLHCID 11706669[2-Chloro-4-(2,4-difluoro-phenylamino)-phenyl]-(2-methyl-5-{1-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-1H-[1,2,3]triazol-4-yl}-phenyl)-methanoneHCID 86605528(5-Azido-2-methyl-phenyl)-[2-chloro-4-(4-fluoro-phenylamino)-phenyl]-methanone

Product 1

HCID 11503327[2-Chloro-4-(4-fluoro-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 101, using compound 433 (1.10 mmol) and 3-butyne-1-ol (1.10 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 foam.

Workup

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

Sources & evidence

ORD record
ord-53d5e3dbb54047d98b3d658dbba302d8
Source dataset
uspto-grants-2012_10
Patent number
US08293772B2

Reaction notes

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