2-Pyridinemethanamine → (R)-2-(3-(3,5-difluorobenzyl)-4-methyl-2-oxoimidazolidin-1-yl)-4-methyl-N-(pyridin-2-ylmethyl)thiazole-5-carboxamide
Reaction equation
N1C=CC=C(CN)C=1.[N:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:15][NH2:16].FC1C=CC(CN2[C@@H](C)CN(C3SC(C(O)=O)=C(C)N=3)C2=O)=CC=1.[F:41][C:42]1[CH:43]=[C:44]([CH:62]=[C:63]([F:65])[CH:64]=1)[CH2:45][N:46]1[C@H:50]([CH3:51])[CH2:49][N:48]([C:52]2[S:53][C:54]([C:58](O)=[O:59])=[C:55]([CH3:57])[N:56]=2)[C:47]1=[O:61]>>[F:65][C:63]1[CH:62]=[C:44]([CH:43]=[C:42]([F:41])[CH:64]=1)[CH2:45][N:46]1[C@H:50]([CH3:51])[CH2:49][N:48]([C:52]2[S:53][C:54]([C:58]([NH:16][CH2:15][C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][N:9]=3)=[O:59])=[C:55]([CH3:57])[N:56]=2)[C:47]1=[O:61]Participants
5
Reactant 4
Product 1
Procedure
Following the procedure as described in Example 2, making variations as required to replace pyridin-3-ylmethanamine with pyridin-2-ylmethanamine and replace (S)-2-(3-(4-fluorobenzyl)-4-methyl-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid with (R)-2-(3-(3,5-difluorobenzyl)-4-methyl-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid, the title compound was obtained as a white solid: mp 147-148° C.; 1H NMR (300 MHz, DMSO-d6) δ 8.55-8.50 (m, 2H), 7.79-7.73 (m, 1H), 7.31-7.24 (m, 2H), 7.19-7.08 (m, 3H), 4.60-4.37 (m, 4H), 4.27-4.20 (m, 1H), 3.88-3.81 (m, 1H), 3.60 (dd, J=10.1, 6.7 Hz, 1H), 2.50 (s, 3H), 1.23 (d, J=6.2 Hz, 3H); MS (ES+) m/z 458.0 (M+1).
Sources & evidence
- ORD record
- ord-8616419a7cf442b4be2d12e71e879d46
- Source dataset
- uspto-grants-2012_11
- Patent number
- US08318949B2
Reaction notes
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