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

HRID 554939Notes

Reaction equation

HRID 554939 reaction equation
FC1C=CC(C[N:7]2C(=O)N(C3SC(C(O)=O)=C(C)N=3)C=N2)=CC=1.[CH2:24]([N:28]1[CH2:32][CH2:31][N:30]([C:33]2[S:34][C:35]([C:39](O)=[O:40])=[C:36]([CH3:38])[N:37]=2)[C:29]1=[O:42])[CH:25]([CH3:27])[CH3:26]>>[CH2:24]([N:28]1[CH2:32][CH2:31][N:30]([C:33]2[S:34][C:35]([C:39]([NH2:7])=[O:40])=[C:36]([CH3:38])[N:37]=2)[C:29]1=[O:42])[CH:25]([CH3:27])[CH3:26]

Participants

3

Reactant 2

HCID 579198022-(1-(4-fluorobenzyl)-5-oxo-1H-1,2,4-triazol-4(5H)-yl)-4-methylthiazole-5-carboxylic acidHCID 579199962-(3-Isobutyl-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid

Product 1

HCID 579198862-(3-Isobutyl-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxamideYield 54%

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-methylthiazole-5-carboxylic acid with 2-(3-isobutyl-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid, the title compound was obtained as a colorless solid in 54% yield: mp: 212-215° C. (methanol/hexanes); 1H NMR (300 MHz, CDCl3) δ 5.69 (s, 2H), 4.13-4.08 (m, 2H), 3.61-3.56 (m, 2H), 3.12 (d, J=7.5 Hz, 2H), 2.60 (s, 3H); 1.97-1.88 (m, 1H), 0.94 (d, J=6.7 Hz, 6H); 13C NMR (75 MHz, CDCl3) δ 165.5, 157.9, 155.6, 153.8, 116.6, 51.5, 42.8, 41.9, 26.7, 19.9, 17.2; MS (ES+) m/z 282.9 M+1).

Sources & evidence

ORD record
ord-1765210af18f4287b7eac34f6410c311
Source dataset
uspto-grants-2011_11
Patent number
US08049016B2

Reaction notes

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