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

HRID 554957Notes

Reaction equation

HRID 554957 reaction equation
N1C=CC=C(CN)C=1.[S:9]1[C:13]([CH2:14][NH2:15])=[CH:12][N:11]=[CH:10]1.[F:16][C:17]1[CH:39]=[CH:38][C:20]([CH2:21][N:22]2[C@@H:26]([CH3:27])[CH2:25][N:24]([C:28]3[S:29][C:30]([C:34](O)=[O:35])=[C:31]([CH3:33])[N:32]=3)[C:23]2=[O:37])=[CH:19][CH:18]=1.FC1C=CC(CN2[C@H](C)CN(C3SC(C(O)=O)=C(C)N=3)C2=O)=CC=1>>[F:16][C:17]1[CH:39]=[CH:38][C:20]([CH2:21][N:22]2[C@H:26]([CH3:27])[CH2:25][N:24]([C:28]3[S:29][C:30]([C:34]([NH:15][CH2:14][C:13]4[S:9][CH:10]=[N:11][CH:12]=4)=[O:35])=[C:31]([CH3:33])[N:32]=3)[C:23]2=[O:37])=[CH:19][CH:18]=1

Participants

5

Reactant 4

HCID 310183-PyridinemethanamineHCID 53040775-(Aminomethyl)-1,3-thiazoleHCID 57919880(R)-2-(3-(4-fluorobenzyl)-4-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 57919791(R)-2-(3-(4-fluorobenzyl)-4-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)-4-methyl-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid the title compound was obtained as a white solid: mp 66-69° C. (hexane); 1H NMR (300 MHz, DMSO-d6) δ 8.93 (s, 1H), 8.62 (t, J=5.7 Hz, 1H), 7.75 (s, 1H), 7.36-7.31 (m, 2H), 7.17-7.12 (m, 2H), 4.58-4.53 (m, 3H), 4.26 (d, J=15.6 Hz, 1H), 4.15 (t, J=9.6 Hz, 1H), 3.74-3.67 (m, 1H), 3.51 (dd, J=10.1, 6.8 Hz, 1H), 2.43 (s, 3H), 1.22 (d, J=6.1 Hz, 3H); MS (ES+) m/z 445.6 (M+1).

Sources & evidence

ORD record
ord-25c811628f2444dda94c81d386adb316
Source dataset
uspto-grants-2011_11
Patent number
US08049016B2

Reaction notes

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