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

HRID 2067265Notes

Reaction equation

HRID 2067265 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]3CCO[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.Cl.C(N)C>>[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][CH3:34])[N:27]=[N:26]2)[CH:22]=[CH:21][C:20]=1[CH3:38])=[O:18]

Participants

4

Reactant 3

HCID 11198Ethylamine hydrochlorideHCID 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}-methanoneHCID 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 11677663[2-Chloro-4-(2,4-difluoro-phenylamino)-phenyl]-{5-[4-(2-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 ethylamine hydrochloride (0.55 mg). 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. 13C NMR (CDCl3) δ 194.8, 159.4 (dd), 155.8 (dd), 148.6, 144.7, 140.8, 138.3, 135.4, 134.6, 133.9, 132.6, 128.2, 124.9 (dd), 124.1 (dd), 122.2, 120.8, 120.4, 116.1, 112.7, 111.7 (dd), 105.0 (dd), 46.5, 42.8, 23.2, 19.9, 12.1

Workup

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

Sources & evidence

ORD record
ord-5a1eb3db9cde4f4296fd8ac9e8c0d8e9
Source dataset
uspto-grants-2012_10
Patent number
US08293772B2

Reaction notes

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