Potassium Hydroxide → N-(3,5-Bis-trifluoromethyl-benzyl)-6-ethynyl-N-methyl-4-o-tolyl-nicotinamide

HRID 1835349Notes

Reaction equation

HRID 1835349 reaction equation
[F:1][C:2]([F:38])([F:37])[C:3]1[CH:4]=[C:5]([CH:30]=[C:31]([C:33]([F:36])([F:35])[F:34])[CH:32]=1)[CH2:6][N:7]([CH3:29])[C:8](=[O:28])[C:9]1[C:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH3:21])=[CH:13][C:12]([C:22]#[C:23][Si](C)(C)C)=[N:11][CH:10]=1.[OH-].[K+].[Cl-].[NH4+]>CO>[F:35][C:33]([F:34])([F:36])[C:31]1[CH:30]=[C:5]([CH:4]=[C:3]([C:2]([F:38])([F:37])[F:1])[CH:32]=1)[CH2:6][N:7]([CH3:29])[C:8](=[O:28])[C:9]1[C:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH3:21])=[CH:13][C:12]([C:22]#[CH:23])=[N:11][CH:10]=1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 25517Ammonium ChlorideHCID 23502795HCID 23502795, compound

Product 1

HCID 23502779N-(3,5-Bis-trifluoromethyl-benzyl)-6-ethynyl-N-methyl-4-o-tolyl-nicotinamideYield 78%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 143 mg (0.261 mmol) N-(3,5-bis-trifluoromethyl-benzyl)-N-methyl-4-o-tolyl-6-trimethylsilanylethynyl-nicotinamide, 2.5 ml of a 1 M aqueous solution of potassium hydroxide and 2.5 ml methanol was stirred at room temperature for 1h. Acidifying to pH 5 with a saturated aqueous solution of ammonium chloride was followed by extraction with three portions of dichloromethane. The combined organic extracts were dried with sodium sulfate and concentrated. Column chromatography afforded 97 mg (78%) of the title compound as a light brown solid.

Workup

  1. extractionwas followed by extraction with three portions of dichloromethane
  2. dry with materialThe combined organic extracts were dried with sodium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-e02041d28c964cebb85875f3b3a8f41b
Source dataset
uspto-grants-2004_08
Patent number
US06770637B2

Reaction notes

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