Dabco → Methyl-phenyl-carbamic Acid 5-(4-trifluoromethyl-benzoylamino)-pyridin-2-yl Ester

HRID 1179944Notes

Reaction equation

HRID 1179944 reaction equation
[OH:1][C:2]1[N:7]=[CH:6][C:5]([NH:8][C:9](=[O:20])[C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.[CH3:21][N:22]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:23](Cl)=[O:24].N12CCN(CC1)CC2>CN(C)C=O>[F:18][C:16]([F:19])([F:17])[C:13]1[CH:12]=[CH:11][C:10]([C:9]([NH:8][C:5]2[CH:4]=[CH:3][C:2]([O:1][C:23](=[O:24])[N:22]([CH3:21])[C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[N:7][CH:6]=2)=[O:20])=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 9237DabcoHCID 77969Carbamic chloride, N-methyl-N-phenyl-HCID 178522253HCID 178522253, compound

Product 1

HCID 69518161Methyl-phenyl-carbamic Acid 5-(4-trifluoromethyl-benzoylamino)-pyridin-2-yl EsterYield 64.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of N-(6-hydroxy-pyridin-3-yl)-4-trifluoromethyl-benzamide (1.41 g, 5.00 mmol), N-methyl-N-phenylcarbamoyl chloride (0.85 g, 5.00 mmol) and 1,4-diazabicyclo[2,2,2]octane (0.56 g, 5.00 mmol) in dimethylformamide (10 mL) was stirred at room temperature overnight. The solvent was evaporated in vacuo and the residue was purified by flash column chromatography (SiO2, ethyl acetate:heptane 50:50) yielding the title compound (1.34 g, 64% yield) as a white solid.

Workup

  1. customThe solvent was evaporated in vacuo
  2. customthe residue was purified by flash column chromatography (SiO2, ethyl acetate:heptane 50:50)

Sources & evidence

ORD record
ord-1d05b5133cc945ae9d66626ca6bca5dd
Source dataset
uspto-grants-2007_10
Patent number
US07279470B2

Reaction notes

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