Pyridine → HCID 71585254, compound

HRID 1500058Notes

Reaction equation

HRID 1500058 reaction equation
[C:1](Cl)(=[O:5])[CH2:2][CH2:3][CH3:4].[Cl-].[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]([C:18]2[N:22]([CH3:23])[N:21]=[C:20]([C:24]([F:30])([F:29])[C:25]([F:28])([F:27])[F:26])[C:19]=2[C:31]([F:34])([F:33])[F:32])=[O:17])=[CH:11][C:10]=1[CH2:35][NH3+:36].N1C=CC=CC=1>C1COCC1>[C:1]([NH:36][CH2:35][C:10]1[CH:11]=[C:12]([NH:15][C:16]([C:18]2[N:22]([CH3:23])[N:21]=[C:20]([C:24]([F:29])([F:30])[C:25]([F:28])([F:26])[F:27])[C:19]=2[C:31]([F:32])([F:33])[F:34])=[O:17])[CH:13]=[CH:14][C:9]=1[Cl:8])(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 1049PyridineHCID 8855Butyryl chlorideHCID 89651137HCID 89651137, compound

Product 1

HCID 71585254HCID 71585254, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Butanoyl chloride (24 mg, 0.23 mmol, 1.1 eq.) in THF (1.5 ml) was added to a solution of [2-chloro-5-({[1-methyl-3-(pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazol-5-yl]carbonyl}amino)phenyl]methanaminium chloride (100 mg, 0.21 mmol) and pyridine (34 mg, 0.43 mmol, 2.1 eq.) in THF (3 ml). After 20 h at room temperature, the mixture was concentrated under reduced pressure and purified by column chromatography on silica gel (hexane/ethyl acetate) to give N-{3-[(butyrylamino)methyl]-4-chlorophenyl}-1-methyl-3-(pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazole-5-carboxamide (80 mg, 75%).

Workup

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

Sources & evidence

ORD record
ord-5a02218f553240fd82930df5a6ab0c34
Source dataset
uspto-grants-2015_12
Patent number
US09204645B2

Reaction notes

Loading…