Pyridine → N-{4-chloro-3-[1-(propionylamino)ethyl]phenyl}-1-methyl-3-(pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazole-5-carboxamide

HRID 1500065Notes

Reaction equation

HRID 1500065 reaction equation
[C:1](Cl)(=[O:4])[CH2:2][CH3:3].[NH2:6][CH:7]([C:9]1[CH:10]=[C:11]([NH:16][C:17]([C:19]2[N:23]([CH3:24])[N:22]=[C:21]([C:25]([F:31])([F:30])[C:26]([F:29])([F:28])[F:27])[C:20]=2[C:32]([F:35])([F:34])[F:33])=[O:18])[CH:12]=[CH:13][C:14]=1[Cl:15])[CH3:8].N1C=CC=CC=1>C1COCC1>[Cl:15][C:14]1[CH:13]=[CH:12][C:11]([NH:16][C:17]([C:19]2[N:23]([CH3:24])[N:22]=[C:21]([C:25]([F:30])([F:31])[C:26]([F:27])([F:28])[F:29])[C:20]=2[C:32]([F:35])([F:34])[F:33])=[O:18])=[CH:10][C:9]=1[CH:7]([NH:6][C:1](=[O:4])[CH2:2][CH3:3])[CH3:8]

Participants

5

Reactant 3

HCID 1049PyridineHCID 62324Propionyl chlorideHCID 89650757N-[3-(1-aminoethyl)-4-chlorophenyl]-1-methyl-3-(pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazole-5-carboxamide

Product 1

HCID 89650770N-{4-chloro-3-[1-(propionylamino)ethyl]phenyl}-1-methyl-3-(pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazole-5-carboxamideYield 90.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Propionyl chloride (21 mg, 0.22 mmol, 1.3 eq.) in THF (1 ml) was added to a solution of N-[3-(1-aminoethyl)-4-chlorophenyl]-1-methyl-3-(pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazole-5-carboxamide (80 mg, 0.17 mmol) and pyridine (18 mg, 0.22 mmol, 1.3 eq.) in THF (3 ml). After 28 h at room temperature, the mixture was concentrated under reduced pressure and purified by column chromatography (hexane/ethyl acetate) to give N-{4-chloro-3-[1-(propionylamino)ethyl]phenyl}-1-methyl-3-(pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazole-5-carboxamide (80 mg, 89%).

Workup

  1. concentrationthe mixture was concentrated under reduced pressure
  2. custompurified by column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-50992c7b9a104d38bd29069b1c26e35d
Source dataset
uspto-grants-2015_12
Patent number
US09204645B2

Reaction notes

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