Pyridine → HCID 18980943, compound

HRID 482614Notes

Reaction equation

HRID 482614 reaction equation
[F:1][C:2]([F:27])([F:26])[C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]([N:12]2[CH2:16][CH:15]([NH:17][CH3:18])[C:14]([C:19]3[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=3)=[N:13]2)=[O:11])=[CH:5][CH:4]=1.[C:28](Cl)(=[O:32])[CH:29]([CH3:31])[CH3:30].N1C=CC=CC=1>C(OCC)(=O)C>[F:27][C:2]([F:1])([F:26])[C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]([N:12]2[CH2:16][CH:15]([N:17]([CH3:18])[C:28](=[O:32])[CH:29]([CH3:31])[CH3:30])[C:14]([C:19]3[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=3)=[N:13]2)=[O:11])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 62325Isobutyryl chlorideHCID 18981009HCID 18981009, compound

Product 1

HCID 18980943HCID 18980943, compoundYield 80.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To 1.8 g (4.5 mmole) of N-(4-trifluoromethylphenyl)-3-(4-chlorophenyl)-4-(N-methylamino)-4,5-dihydro-1H-pyrazole-1-carboxamide (Example 116) in 10 ml of ethyl acetate cooled to 0° C. was added 0.5 g (4.7 mmole) of isobutyryl chloride and 0.4 g of pyridine. After stirring overnight the mixture was diluted with ethyl acetate, washed with water and brine and dried over anhydrous magnesium sulfate. Concentration in vacuo and trituration with diethyl ether gave 1.7 g of the title compound, a white solid, mp 180°-182° C.

Workup

  1. washwashed with water and brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationConcentration in vacuo and trituration with diethyl ether

Sources & evidence

ORD record
ord-09be33dc00fb4dab8633b16a9a991530
Source dataset
uspto-grants-1998_08
Patent number
US05798311

Reaction notes

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