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

HRID 1882377Notes

Reaction equation

HRID 1882377 reaction equation
Br[CH2:2][CH:3]1[CH2:5][C:4]1(F)F.BrCC1CC1.[CH3:13][C:14]1[N:15]=[C:16]([N:24]2[C:28](=[O:29])[NH:27][N:26]=[CH:25]2)[S:17][C:18]=1[C:19]([O:21][CH2:22][CH3:23])=[O:20]>>[CH:5]1([CH2:4][N:27]2[C:28](=[O:29])[N:24]([C:16]3[S:17][C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[C:14]([CH3:13])[N:15]=3)[CH:25]=[N:26]2)[CH2:3][CH2:2]1

Participants

4

Reactant 3

HCID 81503BromomethylcyclopropaneHCID 27614022-(Bromomethyl)-1,1-difluorocyclopropaneHCID 57920013ethyl 4-methyl-2-(5-oxo-1H-1,2,4-triazol-4(5H)-yl)thiazole-5-carboxylate

Product 1

HCID 57919754ethyl 2-(1-(cyclopropylmethyl)-5-oxo-1H-1,2,4-triazol-4(5H)-yl)-4-methylthiazole-5-carboxylateYield 83%

Procedure

Following the procedure as described in Preparation 13, making variation as required to replace bromomethyl-2,2-difluorocyclopropane with (bromomethyl)cyclopropane to react with ethyl 4-methyl-2-(5-oxo-1H-1,2,4-triazol-4(5H)-yl)thiazole-5-carboxylate in place of ethyl 4-methyl-2-(2-oxoimidazolidin-1-yl)thiazole-5-carboxylate, the title compound was obtained as a white solid in 83% yield: 1H NMR (300 MHz, CDCl3) δ 8.27 (s, 1H), 4.31 (q, J=7.1 Hz, 2H), 3.63 (d, J=7.1 Hz, 2H), 2.64 (s, 3H), 1.35 (t, J=7.1 Hz, 3H), 1.19-1.04 (m, 1H), 0.53-0.42 (m, 2H), 0.36-0.27 (m, 2H); MS (ES+) m/z 309.2 (M+1).

Workup

  1. customas described in Preparation 13

Sources & evidence

ORD record
ord-6f483da6e4f8459aa81d25346c573877
Source dataset
uspto-grants-2012_11
Patent number
US08318949B2

Reaction notes

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