2-(1-(4-fluorobenzyl)-5-oxo-1H-1,2,4-triazol-4(5H)-yl)-4-methylthiazole-5-carboxylic acid → (R)-2-(3-(3,5-difluorobenzyl)-4-methyl-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxamide

HRID 1882419Notes

Reaction equation

HRID 1882419 reaction equation
FC1C=CC(C[N:7]2C(=O)N(C3SC(C(O)=O)=C(C)N=3)C=N2)=CC=1.[F:24][C:25]1[CH:26]=[C:27]([CH:45]=[C:46]([F:48])[CH:47]=1)[CH2:28][N:29]1[C@H:33]([CH3:34])[CH2:32][N:31]([C:35]2[S:36][C:37]([C:41]([OH:43])=O)=[C:38]([CH3:40])[N:39]=2)[C:30]1=[O:44]>>[F:24][C:25]1[CH:26]=[C:27]([CH:45]=[C:46]([F:48])[CH:47]=1)[CH2:28][N:29]1[C@H:33]([CH3:34])[CH2:32][N:31]([C:35]2[S:36][C:37]([C:41]([NH2:7])=[O:43])=[C:38]([CH3:40])[N:39]=2)[C:30]1=[O:44]

Participants

3

Reactant 2

HCID 579198022-(1-(4-fluorobenzyl)-5-oxo-1H-1,2,4-triazol-4(5H)-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 57919902(R)-2-(3-(3,5-difluorobenzyl)-4-methyl-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxamide

Procedure

Following the procedure as described in EXAMPLE 1, making variations as required to replace 2-(1-(4-fluorobenzyl)-5-oxo-1H-1,2,4-triazol-4(5H)-yl)-4-methyl-thiazole-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 colorless solid: mp 212-213° C.; 1H NMR (300 MHz, DMSO-d6) δ 7.31 (br s, 2H), 7.18-7.07 (m, 3H), 4.57 (d, J=16.3 Hz, 1H), 4.39 (d, J=16.3 Hz, 1H), 4.22 (dd, J=10.0, 9.1 Hz, 1H), 3.87-3.79 (m, 1H), 3.58 (dd, J=10.0, 6.6 Hz, 1H), 2.46 (s, 3H), 1.22 (d, J=6.2 Hz, 3H); MS (ES+) m/z 366.9 (M+1).

Sources & evidence

ORD record
ord-b5b696efaf3c4a659b1a3486f57a53eb
Source dataset
uspto-grants-2012_11
Patent number
US08318949B2

Reaction notes

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