Pyridine → HCID 89650988, compound

HRID 1500061Notes

Reaction equation

HRID 1500061 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[Cl-].[F:9][C:10]1[C:15]([N:16]([CH3:36])[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:14][CH:13]=[C:12]([F:37])[C:11]=1[CH2:38][NH3+:39].N1C=CC=CC=1>C1COCC1>[C:1]([NH:39][CH2:38][C:11]1[C:10]([F:9])=[C:15]([N:16]([CH3:36])[C:17]([C:19]2[N:23]([CH3:24])[N:22]=[C:21]([C:25]([F:31])([F:30])[C:26]([F:29])([F:27])[F:28])[C:20]=2[C:32]([F:33])([F:34])[F:35])=[O:18])[CH:14]=[CH:13][C:12]=1[F:37])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 89650707HCID 89650707, compound

Product 1

HCID 89650988HCID 89650988, compoundYield 99.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Acetic anhydride (34 mg, 0.34 mmol, 1.3 eq) in THF (1 ml) was added to a solution of [2,6-difluoro-3-(methyl{[1-methyl-3-(pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazol-5-yl]carbonyl}amino)phenyl]methanaminium chloride (130 mg, 0.26 mmol) and pyridine (43 mg, 0.54 mmol, 2.1 eq.) in THF (2.5 ml), and the mixture was left at room temperature for 20 h. After concentration under reduced pressure, the product was purified by column chromatography (hexane/ethyl acetate) to give N-[3-(acetamidomethyl)-2,4-difluorophenyl]-N,1-dimethyl-3-(pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazole-5-carboxamide (131 mg, 99%).

Workup

  1. concentrationAfter concentration under reduced pressure
  2. customthe product was purified by column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-a49605d949d24186bd9b1597aa87990b
Source dataset
uspto-grants-2015_12
Patent number
US09204645B2

Reaction notes

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