Methylamine → 4-((3-(5-acetyl-4-methylthiazol-2-yl)-2-oxoimidazolidin-1-yl)methyl)-N-methylbenzamide
Reaction equation
[CH2:1]([NH2:8])C1C=CC=CC=1.CN.[C:11]([C:14]1[S:18][C:17]([N:19]2[CH2:23][CH2:22][N:21]([CH2:24][C:25]3[CH:33]=[CH:32][C:28]([C:29]([OH:31])=O)=[CH:27][CH:26]=3)[C:20]2=[O:34])=[N:16][C:15]=1[CH3:35])(=[O:13])[CH3:12]>>[C:11]([C:14]1[S:18][C:17]([N:19]2[CH2:23][CH2:22][N:21]([CH2:24][C:25]3[CH:26]=[CH:27][C:28]([C:29]([NH:8][CH3:1])=[O:31])=[CH:32][CH:33]=3)[C:20]2=[O:34])=[N:16][C:15]=1[CH3:35])(=[O:13])[CH3:12]Participants
4
Procedure
Following the procedure as describe in Example 8, making variations as required to replace benzylamine with methylamine to react with 4-((3-(5-acetyl-4-methylthiazol-2-yl)-2-oxoimidazolidin-1-yl)methyl)benzoic acid, the title compound was obtained as a white powder in 43% yield: nip 173-175° C. (ethyl acetate); 1H NMR (300 MHz, CDCl3) δ 7.73 (d, J=8.4 Hz, 2H), 7.35 (d, J=8.4 Hz, 2H), 6.12 (br s, 1H), 4.52 (s, 2H), 4.12-4.06 (m, 2H), 3.49-3.43 (m, 2H), 3.00 (d, J=4.2 Hz, 3H), 2.67 (s, 3H), 2.46 (s, 3H); MS (ES+) m/z 373.2 (M+1).
Sources & evidence
- ORD record
- ord-c585ee4754e74a8eaef06ef53804b0b4
- Source dataset
- uspto-grants-2011_11
- Patent number
- US08063084B2
Reaction notes
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