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

HRID 2067246Notes

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]3[CH2:37][CH2:36]O[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.C(NCC)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][N:32]([CH2:33][CH3:34])[CH2:37][CH3:36])[N:27]=[N:26]2)[CH:22]=[CH:21][C:20]=1[CH3:38])=[O:18]

Participants

Reactant 3

HCID 8021Diethylamine

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 11692166[2-Chloro-4-(2,4-difluoro-phenylamino)-phenyl]-{5-[4-(2-diethylamino-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 diethylamine (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-7969f0d366f246c4b0008aae4a943f06
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08293772B2

Reaction notes

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