3-Pyridinemethanamine → 2-(3-((2,2-difluorocyclopropyl)methyl)-2-oxoimidazolidin-1-yl)-4-methyl-N-(thiazol-5-ylmethyl)thiazole-5-carboxamide
Reaction equation
NCC1C=NC=CC=1.[S:9]1[C:13]([CH2:14][NH2:15])=[CH:12][N:11]=[CH:10]1.[F:16][C:17]1([F:36])[CH2:19][CH:18]1[CH2:20][N:21]1[CH2:25][CH2:24][N:23]([C:26]2[S:27][C:28]([C:32]([OH:34])=O)=[C:29]([CH3:31])[N:30]=2)[C:22]1=[O:35]>>[F:36][C:17]1([F:16])[CH2:19][CH:18]1[CH2:20][N:21]1[CH2:25][CH2:24][N:23]([C:26]2[S:27][C:28]([C:32]([NH:15][CH2:14][C:13]3[S:9][CH:10]=[N:11][CH:12]=3)=[O:34])=[C:29]([CH3:31])[N:30]=2)[C:22]1=[O:35]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 (thiazole-5-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 68% yield: mp 182-184° C.; 1H NMR (300 MHz, DMSO-d6) δ 8.93 (s, 1H), 8.61 (t, J=6.0 Hz, 1H), 7.74 (s, 1H), 4.53 (d, J=6.0 Hz, 1H), 4.01-3.95 (m, 2H), 3.64-3.47 (m, 3H), 3.19-3.12 (m, 1H), 2.44 (s, 3H), 2.04-1.88 (m, 1H), 1.67-1.55 (m, 1H), 1.37-1.26 (m, 1H); MS (ES+) m/z 414.9 (M+1).
Sources & evidence
- ORD record
- ord-5aeb35d919b34fdf998dba9af7463d29
- Source dataset
- uspto-grants-2011_11
- Patent number
- US08049016B2
Reaction notes
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