Potassium Carbonate → 5-(4-Chlorophenyl)-4-cyclopropyl-2-[(5-methyl-1H-imidazol-4-yl)methyl]-2,4-dihydro-3H-1,2,4-triazol-3-one

HRID 714654Notes

Reaction equation

HRID 714654 reaction equation
O[CH2:2][C:3]1[N:4]=[CH:5][NH:6][C:7]=1[CH3:8].[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[N:17]([CH:22]3[CH2:24][CH2:23]3)[C:18](=[O:21])[NH:19][N:20]=2)=[CH:12][CH:11]=1.C(=O)([O-])[O-].[K+].[K+]>>[Cl:9][C:10]1[CH:11]=[CH:12][C:13]([C:16]2[N:17]([CH:22]3[CH2:24][CH2:23]3)[C:18](=[O:21])[N:19]([CH2:2][C:3]3[N:4]=[CH:5][NH:6][C:7]=3[CH3:8])[N:20]=2)=[CH:14][CH:15]=1

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 1224334-hydroxymethyl-5-methyl-1H-imidazoleHCID 580121993-(4-Chlorophenyl)-4-cyclopropyl-1H-1,2,4-triazol-5(4H)-one

Product 1

HCID 699403485-(4-Chlorophenyl)-4-cyclopropyl-2-[(5-methyl-1H-imidazol-4-yl)methyl]-2,4-dihydro-3H-1,2,4-triazol-3-one

Procedure

Analogously to the compound in Example 96A, 181 mg (1.62 mmol) of 4-hydroxymethyl-5-methyl-1H-imidazole, 381 mg (1.62 mmol) of 5-(4-chlorophenyl)-4-cyclopropyl-2,4-dihydro-3H-1,2,4-triazol-3-one [preparation according to WO 2007/134862 Example 36A] and 670 mg (4.85 mmol) of potassium carbonate were reacted with one another. This gave 180 mg (47% of theory) of the target compound in a purity of 76%.

Sources & evidence

ORD record
ord-c218e5f4929e4826a09485f0766a4cb4
Source dataset
uspto-grants-2015_11
Patent number
US09187466B2

Reaction notes

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