Dabco → HCID 69518939, compound

HRID 1831318Notes

Reaction equation

HRID 1831318 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-acf46fa31c564733a1ba19e6c250390b
Source dataset
uspto-grants-2006_06
Patent number
US07067517B2

Reaction notes

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