Water → HCID 69517824, compound

HRID 1179932Notes

Reaction equation

HRID 1179932 reaction equation
Cl.[OH:2][C:3]1[N:8]=[CH:7][C:6]([NH:9][C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)=[O:11])=[CH:5][CH:4]=1.[CH3:18][N:19]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:20](Cl)=[O:21].N12CCN(CC1)CC2.O>CN(C)C=O.ClCCl>[N:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[C:10]([NH:9][C:6]1[CH:5]=[CH:4][C:3]([O:2][C:20](=[O:21])[N:19]([CH3:18])[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[N:8][CH:7]=1)=[O:11]

Participants

7

Reactant 4

HCID 962WaterHCID 9237DabcoHCID 77969Carbamic chloride, N-methyl-N-phenyl-HCID 178479717HCID 178479717, compound

Product 1

HCID 69517824HCID 69517824, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of pyridine-2-carboxylic acid (6-hydroxy-pyridin-3-yl)-amide hydrochloride (0.50 g, 1.99 mmol), N-methyl-N-phenylcarbamoyl chloride (0.44 g, 2.59 mmol) and 1,4-diazabicyclo[2,2,2]octane (0.54 g, 4.81 mmol) in dimethylformamide (15 mL) was stirred at room temperature for 1 hour. Water was added and the solids were isolated by suction, redissolved in dichloromethane. The solution was dried over sodium sulphate, filtered and evaporated in vacuo. The residue was purified by flash column chromatography (SiO2, ethyl acetate:heptane 50:50) yielding the title compound (0.38 g, 55% yield) as a white solid.

Workup

  1. customthe solids were isolated by suction
  2. dry with materialThe solution was dried over sodium sulphate
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. customThe residue was purified by flash column chromatography (SiO2, ethyl acetate:heptane 50:50)

Sources & evidence

ORD record
ord-3159df573e324f3c846f2c04fbefc166
Source dataset
uspto-grants-2007_10
Patent number
US07279470B2

Reaction notes

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