3-Pyridinemethanamine → (R)-2-(3-(4-fluorobenzyl)-5-methyl-2-oxoimidazolidin-1-yl)-4-methyl-N-(thiazol-5-ylmethyl)thiazole-5-carboxamide

HRID 1882439Notes

Reaction equation

HRID 1882439 reaction equation
N1C=CC=C(CN)C=1.[S:9]1[C:13]([CH2:14][NH2:15])=[CH:12][N:11]=[CH:10]1.FC1C=CC(CN2[C@@H](C)CN(C3SC(C(O)=O)=C(C)N=3)C2=O)=CC=1.[F:40][C:41]1[CH:63]=[CH:62][C:44]([CH2:45][N:46]2[CH2:50][C@@H:49]([CH3:51])[N:48]([C:52]3[S:53][C:54]([C:58](O)=[O:59])=[C:55]([CH3:57])[N:56]=3)[C:47]2=[O:61])=[CH:43][CH:42]=1>>[F:40][C:41]1[CH:63]=[CH:62][C:44]([CH2:45][N:46]2[CH2:50][C@@H:49]([CH3:51])[N:48]([C:52]3[S:53][C:54]([C:58]([NH:15][CH2:14][C:13]4[S:9][CH:10]=[N:11][CH:12]=4)=[O:59])=[C:55]([CH3:57])[N:56]=3)[C:47]2=[O:61])=[CH:43][CH:42]=1

Participants

5

Reactant 4

HCID 310183-PyridinemethanamineHCID 53040775-(Aminomethyl)-1,3-thiazoleHCID 57919858(R)-2-(3-(4-fluorobenzyl)-5-methyl-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acidHCID 57919976(S)-2-(3-(4-fluorobenzyl)-4-methyl-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid

Product 1

HCID 57919803(R)-2-(3-(4-fluorobenzyl)-5-methyl-2-oxoimidazolidin-1-yl)-4-methyl-N-(thiazol-5-ylmethyl)thiazole-5-carboxamide

Procedure

Following the procedure as described in EXAMPLE 2, making variations as required to replace pyridin-3-ylmethanamine with thiazol-5-ylmethanamine and replace (S)-2-(3-(4-fluorobenzyl)-4-methyl-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid with (R)-2-(3-(4-fluorobenzyl)-5-methyl-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid, the title compound was obtained as a white solid (67%): mp 70-73° C. (diethyl ether/hexane); 1H NMR (300 MHz, DMSO-ds) δ 8.93 (s, 1H), 8.62 (t, J=5.4 Hz, 1H), 7.76 (s, 1H), 7.33-7.28 (m, 2H), 7.18-7.13 (m, 2H), 4.56-4.39 (m, 5H), 3.59-3.56 (m, 1H), 3.00 (dd, J=9.0, 2.7 Hz, 1H), 2.45 (s, 3H), 1.35 (d, J=6.0 Hz, 3H); MS (ES+) m/z 445.7 (M+1).

Sources & evidence

ORD record
ord-f87819e931824cf7836be7cddfbdec02
Source dataset
uspto-grants-2012_11
Patent number
US08318949B2

Reaction notes

Loading…