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

HRID 1882433Notes

Reaction equation

HRID 1882433 reaction equation
N1C=CC=C(CN)C=1.[CH3:9][C:10]1[N:11]=[CH:12][C:13]([CH2:16][NH2:17])=[N:14][CH:15]=1.FC1C=CC(CN2[C@@H](C)CN(C3SC(C(O)=O)=C(C)N=3)C2=O)=CC=1.[F:42][C:43]1[CH:44]=[C:45]([CH:63]=[C:64]([F:66])[CH:65]=1)[CH2:46][N:47]1[C@H:51]([CH3:52])[CH2:50][N:49]([C:53]2[S:54][C:55]([C:59](O)=[O:60])=[C:56]([CH3:58])[N:57]=2)[C:48]1=[O:62]>>[F:66][C:64]1[CH:63]=[C:45]([CH:44]=[C:43]([F:42])[CH:65]=1)[CH2:46][N:47]1[C@H:51]([CH3:52])[CH2:50][N:49]([C:53]2[S:54][C:55]([C:59]([NH:17][CH2:16][C:13]3[CH:12]=[N:11][C:10]([CH3:9])=[CH:15][N:14]=3)=[O:60])=[C:56]([CH3:58])[N:57]=2)[C:48]1=[O:62]

Participants

5

Reactant 4

HCID 310183-PyridinemethanamineHCID 27564962-(Aminomethyl)-5-methylpyrazineHCID 57919976(S)-2-(3-(4-fluorobenzyl)-4-methyl-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acidHCID 66661653(R)-2-(3-(3,5-difluorobenzyl)-4-methyl-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid

Product 1

HCID 57919817(R)-2-(3-(3,5-difluorobenzyl)-4-methyl-2-oxoimidazolidin-1-yl)-4-methyl-N-((5-methylpyrazin-2-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-methylpyrazin-2-yl)methanamine and replace (S)-2-(3-(4-fluorobenzyl)-4-methyl-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid with (R)-2-(3-(3,5-difluorobenzyl)-4-methyl-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid, the title compound was obtained as a white solid: mp 131-132° C. (ethanol/water); 1H NMR (300 MHz, DMSO-d6) δ 8.58 (t, J=5.7 Hz, 1H), 8.47-8.46 (m, 2H), 7.19-7.08 (m, 3H), 4.60-4.37 (m, 4H), 4.23 (t, J=9.6 Hz, 1H), 3.87-3.80 (m, 1H), 3.59 (dd, J=10.1, 6.7 Hz, 1H), 2.48 (s, 3H), 2.47 (s, 3H), 1.22 (d, J=6.2 Hz, 3H); MS (ES+) m/z 473.0 (M+1).

Sources & evidence

ORD record
ord-9f858e08fb6f4fa48b2cdf42abfbc05a
Source dataset
uspto-grants-2012_11
Patent number
US08318949B2

Reaction notes

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