1,1'-Carbonyldiimidazole → Imidazole-1-carboxylic acid [5-(3-fluoro-4-methanesulfonyl-phenyl)-4-methyl-thiazol-2-yl]-amide

HRID 1672509Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([C:12]2[S:16][C:15]([NH2:17])=[N:14][C:13]=2[CH3:18])[CH:5]=[CH:6][C:7]=1[S:8]([CH3:11])(=[O:10])=[O:9].[C:19](N1C=CN=C1)([N:21]1[CH:25]=[CH:24][N:23]=[CH:22]1)=[O:20]>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([C:12]2[S:16][C:15]([NH:17][C:19]([N:21]3[CH:25]=[CH:24][N:23]=[CH:22]3)=[O:20])=[N:14][C:13]=2[CH3:18])[CH:5]=[CH:6][C:7]=1[S:8]([CH3:11])(=[O:9])=[O:10]

Participants

Conditions

Temperature: 40 °C

Procedure

A suspension of 5-(3-Fluoro-4-methanesulfonyl-phenyl)-4-methyl-thiazol-2-ylamine (17.5 mmol) and 1,1′-carbonyldiimidazole (4.26 g, 26.3 mmol, 1.5 equivalents) in CH2Cl2 (100 ml) was heated at 40° C.-reflux under argon until no starting material remains (30 min-5 hours) as determined by HPLC and NMR. When cool the solid precipitate was removed by filtration.

Workup

temperaturereflux under argon until no starting material
custom(30 min-5 hours)
temperatureWhen cool the solid precipitate
customwas removed by filtration

Sources & evidence

ORD record: ord-a23ba43ad7e740fdb35c4faebe7f8ea5
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07998990B2

Reaction notes

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