ethyl 2-(1-(cyclopropylmethyl)-5-oxo-1H-1,2,4-triazol-4(5H)-yl)-4-methylthiazole-5-carboxylate → 2-(1-(cyclopropylmethyl)-5-oxo-1H-1,2,4-triazol-4(5H)-yl)-4-methylthiazole-5-carboxylic acid

HRID 560756Notes

Reaction equation

HRID 560756 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([N:12]2[C:16](=[O:17])[N:15]([CH2:18][C:19]3[CH:24]=[CH:23]C(C(F)(F)F)=CC=3)[N:14]=[CH:13]2)[S:5][C:6]=1[C:7]([O:9]CC)=[O:8].C1(CN2C(=O)N(C3SC(C(OCC)=O)=C(C)N=3)C=N2)CC1>>[CH:19]1([CH2:18][N:15]2[C:16](=[O:17])[N:12]([C:4]3[S:5][C:6]([C:7]([OH:9])=[O:8])=[C:2]([CH3:1])[N:3]=3)[CH:13]=[N:14]2)[CH2:24][CH2:23]1

Participants

3

Reactant 2

HCID 57919754ethyl 2-(1-(cyclopropylmethyl)-5-oxo-1H-1,2,4-triazol-4(5H)-yl)-4-methylthiazole-5-carboxylateHCID 58031587ethyl 4-methyl-2-(5-oxo-1-(4-(trifluoromethyl)benzyl)-1H-1,2,4-triazol-4(5H)-yl)thiazole-5-carboxylate

Product 1

HCID 579197562-(1-(cyclopropylmethyl)-5-oxo-1H-1,2,4-triazol-4(5H)-yl)-4-methylthiazole-5-carboxylic acidYield 92%

Procedure

Following the procedure as described in Example 20, making variation as required to replace ethyl 4-methyl-2-(5-oxo-1-(4-(trifluoromethyl)benzyl)-1H-1,2,4-triazol-4(5H)-yl)thiazole-5-carboxylate with ethyl 2-(1-(cyclopropylmethyl)-5-oxo-1H-1,2,4-triazol-4(5H)-yl)-4-methylthiazole-5-carboxylate, the title compound was obtained as a white solid in 92% yield: 1H NMR (300 MHz, DMSO-d6) δ 13.39 (br s, 1H), 8.72 (s, 1H), 3.63 (d, J=7.1 Hz, 2H), 2.57 (s, 3H), 1.19-1.04 (m, 1H), 0.53-0.42 (m, 2H), 0.36-0.27 (m, 2H); MS (ES−) m/z 279.0 (M−1).

Sources & evidence

ORD record
ord-eb287069fb0545a08811185962414adb
Source dataset
uspto-grants-2011_11
Patent number
US08063084B2

Reaction notes

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