Dabco → HCID 69518939, compound

HRID 1179942Notes

Reaction equation

HRID 1179942 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:24](=[O:25])[CH2:23][CH2:22][CH2:21][C:20]2=[O:26])=[CH:15][CH:14]=1.N12CCN(CC1)CC2>O1CCCC1>[O:26]=[C:20]1[CH2:21][CH2:22][CH2:23][C:24](=[O:25])[N:19]1[C:16]1[CH:17]=[N:18][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)=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 9237DabcoHCID 77969Carbamic chloride, N-methyl-N-phenyl-HCID 178516110HCID 178516110, compound

Product 1

HCID 69518939HCID 69518939, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of N-methyl-N-phenyl carbamoyl chloride (170 mg, 1.00 mmol), 6′-hydroxy-4,5-dihydro-3H-[1,3]bipyridinyl-2,6-dione (206 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 18 hours. The solvent was evaporated in vacuo and the residue was purified by flash column chromatography (SiO2, first ethyl acetate:heptane 75:25 followed by pure ethyl acetate). Evaporation of the solvent yielded the title compound (260 mg, 77% yield) as a white solid.

Workup

  1. customThe solvent was evaporated in vacuo
  2. customthe residue was purified by flash column chromatography (SiO2, first ethyl acetate:heptane 75:25 followed by pure ethyl acetate)
  3. customEvaporation of the solvent

Sources & evidence

ORD record
ord-35f2f191559f48b9b44b7f18eb8236e7
Source dataset
uspto-grants-2007_10
Patent number
US07279470B2

Reaction notes

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