Potassium Carbonate → N-benzyl-2-(5-benzyl-1H-1,2,4-triazol-3-yl)-4-methylthiazole-5-carboxamide

HRID 2381823Notes

Reaction equation

HRID 2381823 reaction equation
[CH2:1]([NH:8][C:9]([C:11]1[S:15][C:14]([C:16]#[N:17])=[N:13][C:12]=1[CH3:18])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:19]1([CH2:25][C:26]([NH:28][NH2:29])=O)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(=O)([O-])[O-].[K+].[K+]>C(O)CCC>[CH2:1]([NH:8][C:9]([C:11]1[S:15][C:14]([C:16]2[N:17]=[C:26]([CH2:25][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[NH:28][N:29]=2)=[N:13][C:12]=1[CH3:18])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 70301Benzeneacetic acid, hydrazideHCID 68492000N-benzyl-2-cyano-4-methylthiazole-5-carboxamide

Product 1

HCID 68495091N-benzyl-2-(5-benzyl-1H-1,2,4-triazol-3-yl)-4-methylthiazole-5-carboxamideYield 15%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of N-benzyl-2-cyano-4-methylthiazole-5-carboxamide (0.085 g, 0.33 mmol), phenylacetic hydrazide (0.02 g, 0.13 mmol) and potassium carbonate (0.037 g, 0.27 mmol) in 1-butanol (2 mL) was subjected to a microwave irradiation (150° C., 100 W) for 30 minutes. The reaction mixture was purified by column chromatography (0-10% methanol in dichloromethane). Less polar fractions were combined and concentrated in vacuo. The residue was purified by preparative thin layer chromatography plate (60% ethyl acetate in hexanes) to afford the title compound as a yellow solid (0.007 g, 15%): mp 235-237° C.; 1H NMR (300 MHz, DMSO-d6) δ 8.87 (t, J=5.6 Hz, 1H), 7.38-7.21 (m, 11H), 4.43 (d, J=5.6 Hz, 2H), 4.15 (s, 2H), 2.61 (s, 3H); 13C NMR (75 MHz, DMSO-d6) δ 160.8, 156.8, 155.4, 139.1, 136.4, 128.6, 128.6, 128.3, 127.2, 126.8, 42.7, 31.7, 17.0; MS (ES+) m/z 390.3 (M+1).

Workup

  1. customwas subjected to a microwave irradiation (150° C., 100 W) for 30 minutes
  2. customThe reaction mixture was purified by column chromatography (0-10% methanol in dichloromethane)
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by preparative thin layer chromatography plate (60% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-956f5abe12db43e488de950880c851c3
Source dataset
uspto-grants-2012_09
Patent number
US08258160B2

Reaction notes

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