Water → HCID 14170831, compound

HRID 1831308Notes

Reaction equation

HRID 1831308 reaction equation
Cl.[OH:2]C1N=CC(NC(C2C=CC=CN=2)=O)=CC=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>[CH3:18][N:19]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:20](=[O:2])[OH:21]

Participants

7

Reactant 4

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

Product 1

HCID 14170831HCID 14170831, compoundYield 126.3%

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, re-dissolved 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-2e4b611127b3444c8a2b02e96bf75cbf
Source dataset
uspto-grants-2006_06
Patent number
US07067517B2

Reaction notes

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