HCID 11548643, compound → [2-Chloro-4-(2,4-difluoro-phenylamino)-phenyl]-{5-[1-(3-hydroxy-propyl)-1H-[1,2,3]triazol-4-yl]-2-methyl-phenyl}-methanone

HRID 2067196Notes

Reaction equation

ClC1C=C(NC2C=CC(F)=CC=2F)C=CC=1C(C1C=C(C2N=NN(CCO)C=2)C=CC=1C)=O.[Cl:34][C:35]1[CH:40]=[C:39]([NH:41][C:42]2[CH:47]=[CH:46][C:45]([F:48])=[CH:44][C:43]=2[F:49])[CH:38]=[CH:37][C:36]=1[C:50]([C:52]1[CH:57]=[C:56]([C:58]2[N:59]=[N:60][N:61]([CH2:63][CH2:64][CH2:65][O:66]C3CCCCO3)[CH:62]=2)[CH:55]=[CH:54][C:53]=1[CH3:73])=[O:51]>>[Cl:34][C:35]1[CH:40]=[C:39]([NH:41][C:42]2[CH:47]=[CH:46][C:45]([F:48])=[CH:44][C:43]=2[F:49])[CH:38]=[CH:37][C:36]=1[C:50]([C:52]1[CH:57]=[C:56]([C:58]2[N:59]=[N:60][N:61]([CH2:63][CH2:64][CH2:65][OH:66])[CH:62]=2)[CH:55]=[CH:54][C:53]=1[CH3:73])=[O:51]

Participants

Reactant 2

HCID 11548643HCID 11548643, compound

HCID 11612479HCID 11612479, compound

Product 1

HCID 11705730[2-Chloro-4-(2,4-difluoro-phenylamino)-phenyl]-{5-[1-(3-hydroxy-propyl)-1H-[1,2,3]triazol-4-yl]-2-methyl-phenyl}-methanone

Procedure

The reaction was carried out similarly as described in the preparation of compound 102, using compound 103 (0.2 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 colourless foam. 13C NMR (CDCl3) δ 196.1, 159.2 (dd), 155.6 (dd), 148.0, 146.9, 139.9, 137.7, 135.3, 133.8, 131.9, 129.1, 128.0, 127.9, 126.4, 124.5 (dd), 124.3 (dd), 120.3, 116.3, 112.8, 111.6 (dd), 104.9 (dd), 58.8, 47.0, 32.6, 20.2

Workup

customThe crude product was purified by continuous gradient flash chromatography

Sources & evidence

ORD record: ord-da3db75c22f348308e061f76759cc001
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08293772B2

Reaction notes

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