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

HRID 2067248Notes

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]OCC3)[N:27]=[N:26]2)[CH:22]=[CH:21][C:20]=1[CH3:38])=[O:18].Cl[C:40]1C=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(N)CC>>[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][CH2:37][CH2:36][CH3:40])[N:27]=[N:26]2)[CH:22]=[CH:21][C:20]=1[CH3:38])=[O:18]

Participants

Reactant 3

HCID 7852Propylamine

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 11526321[2-Chloro-4-(2,4-difluoro-phenylamino)-phenyl]-{2-methyl-5-[4-(2-propylamino-ethyl)-[1,2,3]triazol-1-yl]-phenyl}-methanone

Procedure

The reaction was carried out similarly as described in the preparation of compound 138, using compound 435 (0.24 mmol) and propylamine (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-14a8e6df36474066ba68bc736124cd03
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08293772B2

Reaction notes

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