3-Pyridinemethanamine → (R)-N-(3,5-difluorobenzyl)-2-(3-(4-fluorobenzyl)-4-methyl-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxamide

HRID 554959Notes

Reaction equation

HRID 554959 reaction equation
N1C=CC=C(CN)C=1.[F:9][C:10]1[CH:11]=[C:12]([CH2:17][NH2:18])[CH:13]=[C:14]([F:16])[CH:15]=1.[F:19][C:20]1[CH:42]=[CH:41][C:23]([CH2:24][N:25]2[C@@H:29]([CH3:30])[CH2:28][N:27]([C:31]3[S:32][C:33]([C:37](O)=[O:38])=[C:34]([CH3:36])[N:35]=3)[C:26]2=[O:40])=[CH:22][CH:21]=1.FC1C=CC(CN2[C@H](C)CN(C3SC(C(O)=O)=C(C)N=3)C2=O)=CC=1>>[F:9][C:10]1[CH:11]=[C:12]([CH:13]=[C:14]([F:16])[CH:15]=1)[CH2:17][NH:18][C:37]([C:33]1[S:32][C:31]([N:27]2[CH2:28][C@@H:29]([CH3:30])[N:25]([CH2:24][C:23]3[CH:41]=[CH:42][C:20]([F:19])=[CH:21][CH:22]=3)[C:26]2=[O:40])=[N:35][C:34]=1[CH3:36])=[O:38]

Participants

5

Reactant 4

HCID 310183-PyridinemethanamineHCID 1452113,5-DifluorobenzylamineHCID 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 57919878(R)-N-(3,5-difluorobenzyl)-2-(3-(4-fluorobenzyl)-4-methyl-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxamide

Procedure

Following the procedure as described in Example 2, making variations as required to replace pyridin-3-ylmethanamine with (3,5-difluorophenyl)methanamine 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 159-160° C. (ethyl acetate/hexane); 1H NMR (300 MHz, DMSO-d6) δ 8.75 (t, J=5.6 Hz, 1H), 7.40-7.35 (m, 2H), 7.21-6.99 (m, 5H), 4.60 (d, J=15.6 Hz, 1H), 4.39 (d, J=5.6 Hz, 2H), 4.30 (d, J=15.6 Hz, 1H), 4.20 (dd, J=10.1, 9.1 Hz, 1H), 3.78-3.71 (m, 1H), 3.56 (dd, J=10.2, 6.8 Hz, 1H), 2.48 (s, 3H), 1.22 (d, J=6.1 Hz, 3H); MS (ES+) m/z 474.9 (M+1).

Sources & evidence

ORD record
ord-e5c24f09024146408fb820592ddc8314
Source dataset
uspto-grants-2011_11
Patent number
US08049016B2

Reaction notes

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