2,4-Difluorophenyl isocyanate → N-(5-{6-Chloro-5-[3-(2,4-difluorophenyl)ureido]-pyridin-3-yl}-4-methyl-1,3-thiazol-2-yl)acetamide

HRID 252726Notes

Reaction equation

[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N:9]=[C:10]=[O:11].[NH2:12][C:13]1[CH:14]=[C:15]([C:20]2[S:24][C:23]([NH:25][C:26](=[O:28])[CH3:27])=[N:22][C:21]=2[CH3:29])[CH:16]=[N:17][C:18]=1[Cl:19]>C1COCC1>[Cl:19][C:18]1[N:17]=[CH:16][C:15]([C:20]2[S:24][C:23]([NH:25][C:26](=[O:28])[CH3:27])=[N:22][C:21]=2[CH3:29])=[CH:14][C:13]=1[NH:12][C:10]([NH:9][C:3]1[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=1[F:1])=[O:11]

Participants

Conditions

Temperature: 50 °C

Procedure

2,4-Difluorophenyl isocyanate (0.022 mL) was added to a stirred solution of N-[5-(5-amino-6-chloropyridin-3-yl)-4-methyl-1,3-thiazol-2-yl]acetamide (50 mg) in THF (1 mL) and the resultant solution was stirred and heated to 50° C. for 1 hour. The mixture was cooled to room temperature and concentrated by evaporation. The residue was purified by preparative HPLC. There was thus obtained the title compound as a white solid (20 mg); 1H NMR Spectrum: (DMSOd6) 2.16 (s, 3H), 2.39 (s, 3H), 7.05-7.08 (m, 1H), 7.33-7.37 (m, 1H), 8.09-8.14 (m, 1H), 8.17 (s, 1H), 8.67 (m, 1H), 8.67 (s, 1H), 9.48 (s, 1H); Mass Spectrum: M+H+ 438.

Workup

temperatureThe mixture was cooled to room temperature
concentrationconcentrated by evaporation
customThe residue was purified by preparative HPLC

Sources & evidence

ORD record: ord-4ef8fb1d0f614468ae1c18cf39b661db
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07868188B2

Reaction notes

Loading…