Ammonium Chloride → 2-(1-((2,2-difluorocyclopropyl)methyl)-5-oxo-1H-1,2,4-triazol-4(5H)-yl)-4-methylthiazole-5-carboxamide

HRID 555014Notes

Reaction equation

HRID 555014 reaction equation
FC1(F)CC1C[N:6]1CCN(C2SC(C(O)=O)=C(C)N=2)C1=O.[F:22][C:23]1([F:42])[CH2:25][CH:24]1[CH2:26][N:27]1[C:31](=[O:32])[N:30]([C:33]2[S:34][C:35]([C:39](O)=[O:40])=[C:36]([CH3:38])[N:37]=2)[CH:29]=[N:28]1.[Cl-].[NH4+]>>[F:22][C:23]1([F:42])[CH2:25][CH:24]1[CH2:26][N:27]1[C:31](=[O:32])[N:30]([C:33]2[S:34][C:35]([C:39]([NH2:6])=[O:40])=[C:36]([CH3:38])[N:37]=2)[CH:29]=[N:28]1

Participants

4

Reactant 3

HCID 25517Ammonium ChlorideHCID 441923722-(1-((2,2-difluorocyclopropyl)methyl)-5-oxo-1H-1,2,4-triazol-4(5H)-yl)-4-methylthiazole-5-carboxylic acidHCID 579198122-(3-((2,2-Difluorocyclopropyl)methyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid

Product 1

HCID 579199222-(1-((2,2-difluorocyclopropyl)methyl)-5-oxo-1H-1,2,4-triazol-4(5H)-yl)-4-methylthiazole-5-carboxamideYield 62%

Procedure

Following the procedure as describe in Example 16, making variations as required to replace 2-(3-((2,2-difluorocyclopropyl)methyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid with 2-(1-((2,2-difluorocyclopropyl)methyl)-5-oxo-1H-1,2,4-triazol-4(5H)-yl)-4-methylthiazole-5-carboxylic acid to react with ammonium chloride, the title compound was obtained as a colourless solid in 62% yield: mp 273-275° C.; 1H NMR (300 MHz, DMSO-d6) δ 8.74 (s, 1H), 7.60 (br, 2H), 4.02-3.79 (m, 2H), 2.52 (s, 3H), 2.20-2.05 (m, 1H), 1.72-1.60 (m, 1H), 1.48-1.37 (m, 1H); 13C NMR (75 MHz, DMSO-d6) δ 163.1, 151.7, 151.4, 150.0, 132.4, 123.5, 114.4 (t), 42.7 (d), 20.8, 17.3, 14.9; MS (ES+) m/z 316.0 (M+1).

Sources & evidence

ORD record
ord-1efcbf5bc4c149f0a148dc19ac53a519
Source dataset
uspto-grants-2011_11
Patent number
US08049016B2

Reaction notes

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