3-Pyridinemethanamine → (S)-2-(3-(4-fluorobenzyl)-5-methyl-2-oxoimidazolidin-1-yl)-4-methyl-N-((5-methylisoxazol-3-yl)methyl)thiazole-5-carboxamide

HRID 554966Notes

Reaction equation

HRID 554966 reaction equation
N1C=CC=C(CN)C=1.[CH3:9][C:10]1[O:14][N:13]=[C:12]([CH2:15][NH2:16])[CH:11]=1.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:64]=[CH:63][C:45]([CH2:46][N:47]2[CH2:51][C@H:50]([CH3:52])[N:49]([C:53]3[S:54][C:55]([C:59](O)=[O:60])=[C:56]([CH3:58])[N:57]=3)[C:48]2=[O:62])=[CH:44][CH:43]=1>>[F:41][C:42]1[CH:64]=[CH:63][C:45]([CH2:46][N:47]2[CH2:51][C@H:50]([CH3:52])[N:49]([C:53]3[S:54][C:55]([C:59]([NH:16][CH2:15][C:12]4[CH:11]=[C:10]([CH3:9])[O:14][N:13]=4)=[O:60])=[C:56]([CH3:58])[N:57]=3)[C:48]2=[O:62])=[CH:44][CH:43]=1

Participants

5

Reactant 4

HCID 310183-PyridinemethanamineHCID 27763061-(5-Methyl-1,2-oxazol-3-yl)methanamineHCID 57919852(S)-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 57919935(S)-2-(3-(4-fluorobenzyl)-5-methyl-2-oxoimidazolidin-1-yl)-4-methyl-N-((5-methylisoxazol-3-yl)methyl)thiazole-5-carboxamide

Procedure

Following the procedure as described in Example 2, making variations as required to replace pyridin-3-ylmethanamine with (5-methylisoxazol-3-yl)methanamine and replace (S)-2-(3-(4-fluorobenzyl)-4-methyl-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid with (S)-2-(3-(4-fluorobenzyl)-5-methyl-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid, the title compound was obtained as a white solid (70%): mp 174-175° C. (N,N-dimethylformamide/water); 1H NMR (300 MHz, DMSO-d6) δ 8.48 (t, J=5.8 Hz, 1H), 7.37-7.32 (m, 2H), 7.23-7.17 (m, 2H), 6.13 (d, J=0.7 Hz, 1H), 4.58-4.52 (m, 1H), 4.43 (d, J=4.3 Hz, 2H), 4.36 (d, J=5.8 Hz, 2H), 3.64-3.58 (m, 1H), 3.04 (dd, J=9.0, 3.4 Hz, 1H), 2.48 (s, 3H), 2.37 (d, J=0.7 Hz, 3H), 1.39 (d, J=6.0 Hz, 3H); MS (ES+) m/z 443.8 (M+1).

Sources & evidence

ORD record
ord-3edb393ed4824384ae7041a22ff75f12
Source dataset
uspto-grants-2011_11
Patent number
US08049016B2

Reaction notes

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