Water → HCID 178480486, compound

HRID 908101Notes

Reaction equation

[C:1]1([NH:7][NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:9]12[CH2:15][CH:12]([CH2:13][CH2:14]1)[CH2:11][CH:10]2[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[NH:22][C:23]([C:25]1[C:26]([CH:31]([F:33])[F:32])=[N:27][N:28]([CH3:30])[CH:29]=1)=S.O.C1CCCCC1.C(OCC)(=O)C>CN(C)C=O.CO>[CH:9]12[CH2:15][CH:12]([CH2:13][CH2:14]1)[CH2:11][CH:10]2[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[NH:22][C:23]([C:25]1[C:26]([CH:31]([F:33])[F:32])=[N:27][N:28]([CH3:30])[CH:29]=1)=[N:8][NH:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 70 °C

Procedure

0.9 g (8.4 mmol) of phenylhydrazine in 10 ml of dimethylformamide is added to a solution consisting of 1.0 g (2.7 mmol) of N-(2-bicyclo[2.2.1]hept-2-ylphenyl)-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-thiocarboxamide in 10 ml of methanol. The reaction mixture is stirred at 70° C. for 16 hours. For work-up, the reaction mixture is poured into water and extracted three times with in each case 20 ml of dichloromethane. The combined organic phases are dried over sodium sulphate and concentrated under reduced pressure. Column chromatography (gradient cyclohexane/ethyl acetate) gives 0.42 g (0.96 mmol, 35% of theory) of N-(2-bicyclo[2.2.1]hept-2-ylphenyl)-3-(difluoromethyl)-1-methyl-N′-phenyl-1H-pyrazole-4-carbohydrazonamide [logP (pH 2.3)=3.66].

Workup

extractionextracted three times with in each case 20 ml of dichloromethane
dry with materialThe combined organic phases are dried over sodium sulphate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-8617f6486b9d487f9c3eac423191cf5d
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08017558B2

Reaction notes

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