3-Pyridinemethanamine → 2-(3-((2,2-difluorocyclopropyl)methyl)-2-oxoimidazolidin-1-yl)-4-methyl-N-((4-methylthiazol-2-yl)methyl)thiazole-5-carboxamide
Reaction equation
[NH2:1][CH2:2]C1C=NC=CC=1.C[C:10]1([CH2:15]N)[CH2:14][S:13][CH:12]=[N:11]1.[F:17][C:18]1([F:37])[CH2:20][CH:19]1[CH2:21][N:22]1[CH2:26][CH2:25][N:24]([C:27]2[S:28][C:29]([C:33]([OH:35])=O)=[C:30]([CH3:32])[N:31]=2)[C:23]1=[O:36]>>[F:37][C:18]1([F:17])[CH2:20][CH:19]1[CH2:21][N:22]1[CH2:26][CH2:25][N:24]([C:27]2[S:28][C:29]([C:33]([NH:1][CH2:2][C:12]3[S:13][CH:14]=[C:10]([CH3:15])[N:11]=3)=[O:35])=[C:30]([CH3:32])[N:31]=2)[C:23]1=[O:36]Participants
4
Reactant 3
Product 1
Procedure
Following the procedure as describe in Example 16, making variations as required to replace 3-(aminomethyl)pyridine with 1-(4-methyl-1,3-thiazole-4-yl)methylamine to react with 2-(3-((2,2-difluorocyclopropyl)methyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid, the title compound was obtained as a colourless solid in 77% yield: mp 157-159° C.; 1H NMR (300 MHz, DMSO-d6) δ 8.42 (t, J=6.0 Hz, 1H), 7.11 (s, 1H), 4.36 (d, J=6.0 Hz, 1H), 4.02-3.96 (m, 2H), 3.64-3.47 (m, 3H), 3.20-3.12 (m, 1H), 2.59 (s, 3H), 2.44 (s, 3H), 2.04-1.89 (m, 1H), 1.68-1.55 (m, 1H), 1.37-1.26 (m, 1H); MS (ES+) m/z 428.9 (M+1).
Sources & evidence
- ORD record
- ord-814b68d8257a4d528438b18bce610a1c
- Source dataset
- uspto-grants-2012_11
- Patent number
- US08318949B2
Reaction notes
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