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

HRID 2067247Notes

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]=2[F:16])[CH:5]=[CH:4][C:3]=1[C:17]([C:19]1[CH:24]=[C:23]([N:25]2[CH:29]=[C:28]([CH2:30][CH2:31][N:32]3CC[O:35][CH2:34][CH2:33]3)[N:27]=[N:26]2)[CH:22]=[CH:21][C:20]=1[CH3:38])=[O:18].ClC1C=C(NC2C=CC(F)=CC=2F)C=CC=1C(C1C=C(N2C=C(CCOS(C3C=CC(C)=CC=3)(=O)=O)N=N2)C=CC=1C)=O.NCCO>>[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]=2[F:16])[CH:5]=[CH:4][C:3]=1[C:17]([C:19]1[CH:24]=[C:23]([N:25]2[CH:29]=[C:28]([CH2:30][CH2:31][NH:32][CH2:33][CH2:34][OH:35])[N:27]=[N:26]2)[CH:22]=[CH:21][C:20]=1[CH3:38])=[O:18]

Participants

Reactant 3

HCID 700Ethanolamine

HCID 11692340[2-Chloro-4-(2,4-difluoro-phenylamino)-phenyl]-{2-methyl-5-[4-(2-morpholin-4-yl-ethyl)-[1,2,3]triazol-1-yl]-phenyl}-methanone

HCID 86605530Toluene-4-sulfonic acid 2-(1-{3-[2-chloro-4-(2,4-difluoro-phenylamino)-benzoyl]-4-methyl-phenyl}-1H-[1,2,3]triazol-4-yl)-ethyl ester

Product 1

HCID 11577112[2-Chloro-4-(2,4-difluoro-phenylamino)-phenyl]-(5-{4-[2-(2-hydroxy-ethylamino)-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 138, using compound 435 (0.24 mmol) and 2-amino-ethanol (0.5 mL). The crude product was purified by continuous gradient flash chromatography using MeOH/DCM 0:100 to 15:85 as the eluent to afford the title compound as yellow foam.

Workup

customThe crude product was purified by continuous gradient flash chromatography

Sources & evidence

ORD record: ord-805aa4db7d654b8f9ddb3078467d87bf
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08293772B2

Reaction notes

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