Dabco → HCID 69519728, compound

HRID 1831319Notes

Reaction equation

HRID 1831319 reaction equation
[CH3:1][N:2]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[C:3](Cl)=[O:4].[OH:12][C:13]1[N:18]=[CH:17][C:16]([N:19]2[C:23](=[O:24])[CH2:22][CH2:21][C:20]2=[O:25])=[CH:15][CH:14]=1.N12CCN(CC1)CC2>O1CCCC1>[O:25]=[C:20]1[CH2:21][CH2:22][C:23](=[O:24])[N:19]1[C:16]1[CH:15]=[CH:14][C:13]([O:12][C:3](=[O:4])[N:2]([CH3:1])[C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)=[N:18][CH:17]=1

Participants

5

Reactant 3

HCID 9237DabcoHCID 77969Carbamic chloride, N-methyl-N-phenyl-HCID 178516286HCID 178516286, compound

Product 1

HCID 69519728HCID 69519728, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of N-methyl-N-phenyl carbamoyl chloride (170 mg, 1.00 mmol), 1-(6-hydroxy-pyridin-3-yl)-pyrrolidine-2,5-dione (192 mg, 1.00 mmol) and 1,4-diazabicyclo[2,2,2]octane (112 mg, 1.00 mmol) in tetrahydrofuran (10 mL) was stirred at room temperature for 4 hours. The solvent was evaporated in vacuo and the residue was purified by flash column chromatography (SiO2, ethyl acetate:heptane 80:20) yielding the title compound (275 mg, 85% 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 80:20)

Sources & evidence

ORD record
ord-c8f09738dda34fe983a4ae6720adc03d
Source dataset
uspto-grants-2006_06
Patent number
US07067517B2

Reaction notes

Loading…