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

HRID 554958Notes

Reaction equation

HRID 554958 reaction equation
N1C=CC=C(CN)C=1.[CH3:9][C:10]1[CH:14]=[C:13]([CH2:15][NH2:16])[NH:12][N:11]=1.[F:17][C:18]1[CH:40]=[CH:39][C:21]([CH2:22][N:23]2[C@@H:27]([CH3:28])[CH2:26][N:25]([C:29]3[S:30][C:31]([C:35](O)=[O:36])=[C:32]([CH3:34])[N:33]=3)[C:24]2=[O:38])=[CH:20][CH:19]=1.FC1C=CC(CN2[C@H](C)CN(C3SC(C(O)=O)=C(C)N=3)C2=O)=CC=1>>[F:17][C:18]1[CH:40]=[CH:39][C:21]([CH2:22][N:23]2[C@H:27]([CH3:28])[CH2:26][N:25]([C:29]3[S:30][C:31]([C:35]([NH:16][CH2:15][C:13]4[NH:12][N:11]=[C:10]([CH3:9])[CH:14]=4)=[O:36])=[C:32]([CH3:34])[N:33]=3)[C:24]2=[O:38])=[CH:20][CH:19]=1

Participants

5

Reactant 4

HCID 310183-PyridinemethanamineHCID 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 acidHCID 178426643HCID 178426643, compound

Product 1

HCID 178426590(R)-2-(3-(4-fluorobenzyl)-4-methyl-2-oxoimidazolidin-1-yl)-4-methyl-N-((3-methyl-1H-pyrazol-5-yl)methyl)thiazole-5-carboxamide

Procedure

Following the procedure as described in Example 2, making variations as required to replace pyridin-3-ylmethanamine with (3-methyl-1H-pyrazol-5-yl)-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 215-216° C. (ethyl acetate); 1H NMR (300 MHz, DMSO-d6) δ 12.22 (s, 1H), 8.31 (br, 1H), 7.40-7.35 (m, 2H), 7.22-7.16 (m, 2H), 5.89 (s, 1H), 4.59 (d, J=15.5 Hz, 1H), 4.33-4.16 (m, 4H), 3.78-3.71 (m, 1H), 3.55 (dd, J=10.1, 6.8 Hz, 1H), 2.46 (s, 3H), 2.17 (s, 3H), 1.22 (d, J=6.1 Hz, 3H); MS (ES+) m/z 442.9 (M+1).

Sources & evidence

ORD record
ord-67b1a14a6d1c447798d599ccc88042f7
Source dataset
uspto-grants-2011_11
Patent number
US08049016B2

Reaction notes

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