Benzylamine → 3-((3-(5-acetyl-4-methylthiazol-2-yl)-2-oxoimidazolidin-1-yl)methyl)-N-methylbenzamide
Reaction equation
[CH2:1]([NH2:8])C1C=CC=CC=1.Cl.CN.[C:12]([C:15]1[S:19][C:18]([N:20]2[CH2:24][CH2:23][N:22]([CH2:25][C:26]3[CH:27]=[C:28]([CH:32]=[CH:33][CH:34]=3)[C:29]([OH:31])=O)[C:21]2=[O:35])=[N:17][C:16]=1[CH3:36])(=[O:14])[CH3:13]>>[C:12]([C:15]1[S:19][C:18]([N:20]2[CH2:24][CH2:23][N:22]([CH2:25][C:26]3[CH:27]=[C:28]([CH:32]=[CH:33][CH:34]=3)[C:29]([NH:8][CH3:1])=[O:31])[C:21]2=[O:35])=[N:17][C:16]=1[CH3:36])(=[O:14])[CH3:13]Participants
4
Procedure
Following the procedure as describe in Example 8, making variations as required to replace benzylamine with methylamine monohydrochloride to react with 3-((3-(5-acetyl-4-methylthiazol-2-yl)-2-oxoimidazolidin-1-yl)methyl)benzoic acid, the title compound was obtained as a white powder in 85% yield: 1H NMR (300 MHz, CDCl3) δ 7.73-7.62 (m, 2H), 7.42-7.34 (m, 2H), 6.32 (br s, 1H), 4.51 (s, 2H), 4.13-4.04 (m, 2H), 3.49-3.41 (m, 2H), 2.97 (d, J=4.8 Hz, 3H), 2.60 (s, 3H), 2.45 (s, 3H); MS (ES+) m/z 373.1 (M+1).
Sources & evidence
- ORD record
- ord-6698291280214463b32a5f27e34dc985
- Source dataset
- uspto-grants-2012_10
- Patent number
- US08293768B2
Reaction notes
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