3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzohydrazide → ethyl 8-(3,4-difluorophenyl)-3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine-8-carboxylate

HRID 1398172Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[N:13]1[CH:17]=[C:16]([CH3:18])[N:15]=[CH:14]1)[C:6]([NH:8][NH2:9])=O.[F:19][C:20]1[CH:21]=[C:22]([C:27]2([C:35]([O:37][CH2:38][CH3:39])=[O:36])[CH2:32][CH2:31][CH2:30][N:29]=[C:28]2SC)[CH:23]=[CH:24][C:25]=1[F:26]>C(O)C.C(OCC)(=O)C>[F:19][C:20]1[CH:21]=[C:22]([C:27]2([C:35]([O:37][CH2:38][CH3:39])=[O:36])[CH2:32][CH2:31][CH2:30][N:29]3[C:6]([C:5]4[CH:10]=[CH:11][C:12]([N:13]5[CH:17]=[C:16]([CH3:18])[N:15]=[CH:14]5)=[C:3]([O:2][CH3:1])[CH:4]=4)=[N:8][N:9]=[C:28]23)[CH:23]=[CH:24][C:25]=1[F:26]

Participants

Conditions

Temperature: 90 °C

Procedure

3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)benzohydrazide (236 mg) was added to a mixture of ethyl 3-(3,4-difluorophenyl)-2-(methylsulfanyl)-3,4,5,6-tetrahydropyridine-3-carboxylate (300 mg) in ethanol (3 mL) at room temperature, and the mixture was stirred at 90° C. for 2 days. The reaction mixture was diluted with ethyl acetate, the mixture was washed with water and saturated brine and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane) to give the title compound (217 mg).

Workup

washthe mixture was washed with water and saturated brine
dry with materialdried over anhydrous sodium sulfate
customthe solvent was evaporated under reduced pressure
customThe residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane)

Sources & evidence

ORD record: ord-0835a7a82d6442fea10806d37bb56315
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08901309B2

Reaction notes

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