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

HRID 1179948Notes

Reaction equation

HRID 1179948 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.[CH3:19][N:20]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:21](Cl)=[O:22].N12CCN(CC1)CC2.O>CN(C)C=O.CCCCCCC>[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:21](=[O:22])[N:20]([CH3:19])[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[N:7][CH:6]=2)=[O:18])=[CH:11][CH:12]=1

Participants

7

Reactant 4

HCID 962WaterHCID 9237DabcoHCID 77969Carbamic chloride, N-methyl-N-phenyl-HCID 178491588HCID 178491588, compound

Product 1

HCID 69519091Methyl-phenyl-carbamic acid 5-(4-methoxy-benzoylamino)-pyridin-2-yl esterYield 57.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8900HeptaneSolvent

Procedure

A solution of N-(6-hydroxy-pyridin-3-yl)-4-methoxy-benzamide (1.22 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 (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-200edd488b2a4c1193fc1f0422c8e37b
Source dataset
uspto-grants-2007_10
Patent number
US07279470B2

Reaction notes

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