N-Benzyl-2-imino-4-methyl-2,3-dihydro-1,3-thiazole-5-carboximidic acid → 2-(5-Chloro-2-fluorobenzoylamino)-4-methylthiazole-5-carboxylic Acid Benzylamide
Reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([F:11])=[C:6]([CH:10]=1)[C:7](Cl)=[O:8].[CH2:12]([NH:19][C:20]([C:22]1[S:26][C:25]([NH2:27])=[N:24][C:23]=1[CH3:28])=[O:21])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>>[CH2:12]([NH:19][C:20]([C:22]1[S:26][C:25]([NH:27][C:7](=[O:8])[C:6]2[CH:10]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=2[F:11])=[N:24][C:23]=1[CH3:28])=[O:21])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1Participants
3
Procedure
Following the procedure as described in Example 2, making variations only as required to use 5-chloro-2-fluorobenzoyl chloride in place of benzoyl chloride to react with 2-amino-4-methylthiazole-5-carboxylic acid benzylamide, the title compound was obtained as a white solid in 22% yield. m.p. 175-178° C.; 1H NMR (CDCl3, 300 MHz) δ 8.12 (dd, J=2.8, 6.6 Hz, 1H), 7.53 (ddd, J=2.8, 4.4, 8.8 Hz, 1H), 7.38-7.24 (m, 6H), 7.17 (dd, J=8.8, 11.3 Hz, 1H), 6.01 (t, J=4.7 Hz, 1H), 4.59 (d, J=5.6 Hz, 2H), 2.61 (s, 3H); MS (ES+) m/z 404.1 (M+1).
Sources & evidence
- ORD record
- ord-6d39dc4103ab40e8a33f5d3cf6748415
- Source dataset
- uspto-grants-2013_09
- Patent number
- US08541457B2
Reaction notes
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