Diisopropylethylamine → 1-(2-Fluoro-4-methanesulfonylphenyl)-1H-imidazole-4-carboxylic acid

HRID 1409731Notes

Reaction equation

[NH:1]1[CH:5]=[C:4]([C:6]([OH:8])=[O:7])[N:3]=[CH:2]1.F[C:10]1[CH:15]=[CH:14][C:13]([S:16]([CH3:19])(=[O:18])=[O:17])=[CH:12][C:11]=1[F:20].C(N(CC)C(C)C)(C)C>CN(C)C=O>[F:20][C:11]1[CH:12]=[C:13]([S:16]([CH3:19])(=[O:18])=[O:17])[CH:14]=[CH:15][C:10]=1[N:1]1[CH:5]=[C:4]([C:6]([OH:8])=[O:7])[N:3]=[CH:2]1

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 1H-imidazole-4-carboxylic acid (500 mg), 1,2-difluoro-4-methanesulfonylbenzene (1.2 g), and N,N-diisopropyl-ethyl-amine (4 mL) in N,N-dimethylformamide (6 mL) is heated to 120° C. overnight. The crude product is purified by HPLC. LC (method 20): tR=1.69 min; Mass spectrum (APCI): m/z=285 [M+H]+.

Workup

customThe crude product is purified by HPLC

Sources & evidence

ORD record: ord-3ed85d0efecc41b0a3b6ab6f27e9acf9
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08921398B2

Reaction notes

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