Water → Methyl-phenyl-carbamic acid 5-(4-methoxy-benzoylamino)-pyridin-2-yl ester

HRID 1831324Notes

Reaction equation

HRID 1831324 reaction equation
[OH:1][C:2]1[N:7]=[CH:6][C:5]([NH:8][C:9](=[O:18])[C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.N12C[CH2:25][N:22]([CH2:23][CH2:24]1)[CH2:21]C2.[OH2:27].[CH3:28][CH2:29][CH2:30][CH2:31]CCC>CN(C)C=O>[CH3:17][O:16][C:13]1[CH:14]=[CH:15][C:10]([C:9]([NH:8][C:5]2[CH:4]=[CH:3][C:2]([O:1][C:25](=[O:27])[N:22]([CH3:21])[C:23]3[CH:24]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[N:7][CH:6]=2)=[O:18])=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8900HeptaneHCID 9237DabcoHCID 178491588HCID 178491588, compound

Product 1

HCID 69519091Methyl-phenyl-carbamic acid 5-(4-methoxy-benzoylamino)-pyridin-2-yl esterYield 57%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of N-(6-hydroxy-pyridin-3-yl)-4-methoxy-benzamide (1.22 g, 5.00 mmol), N-methyl-N-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 (20 mL) was stirred at room temperature for 2 hours. Water (100 mL) was added. The solids were isolated by suction and washed with water. Crystallisation from ethyl acetate:heptane yielded the title compound (1.08 g, 57% yield).

Workup

  1. customThe solids were isolated by suction
  2. washwashed with water
  3. customCrystallisation from ethyl acetate

Sources & evidence

ORD record
ord-b5805cf902794f5ba18745c110713f43
Source dataset
uspto-grants-2006_06
Patent number
US07067517B2

Reaction notes

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