Hydrochloric Acid → HCID 67954717, compound

HRID 1258889Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[N:10][N:11]([CH3:18])[C:12]=2[C:13]2[N:14]=[CH:15][NH:16][CH:17]=2)=[CH:4][CH:3]=1.Cl[C:20]1[CH:29]=[CH:28][C:23]([C:24]([O:26][CH3:27])=[O:25])=[CH:22][N:21]=1.C(=O)([O-])[O-].[K+].[K+].Cl>CN(C=O)C>[CH3:27][O:26][C:24](=[O:25])[C:23]1[CH:28]=[CH:29][C:20]([N:16]2[CH:17]=[C:13]([C:12]3[N:11]([CH3:18])[N:10]=[N:9][C:8]=3[C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)[N:14]=[CH:15]2)=[N:21][CH:22]=1

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 4-(4-fluoro-phenyl)-5-(1H-imidazol-4-yl)-1-methyl-1H-[1,2,3]triazole (82 mg, 0.34 mmol), methyl 6-chloronicotinate (58 mg, 0.34 mmol) and potassium carbonate (93 mg, 0.67 mmol) in DMF (1.7 mL) was stirred under Ar in a sealed flask and heated at 120° C. for 16 h. After cooling to room temperature the mixture was poured into HCl (1 N) and extracted with ethyl acetate and the combined extracts washed with water, brine, dried over sodium sulphate, filtered and evaporated. Purification by chromatography (silica, 0 to 100% ethyl acetate in heptane) afforded the title compound (70 mg, 55%) as an off white solid. MS: m/e=379.2 [M+H]+.

Workup

temperatureAfter cooling to room temperature the mixture
extractionextracted with ethyl acetate
washthe combined extracts washed with water, brine
dry with materialdried over sodium sulphate
filtrationfiltered
customevaporated
customPurification by chromatography (silica, 0 to 100% ethyl acetate in heptane)

Sources & evidence

ORD record: ord-bb8f735c5bf649c3835504ac5397add0
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08466181B2

Reaction notes

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