Dabco → Carbamic acid, methylphenyl-, 5-[[(2,2-dimethylpropyl)amino]carbonyl]-2-pyridinyl ester

HRID 1179935Notes

Reaction equation

HRID 1179935 reaction equation
[CH3:1][C:2]([CH3:15])([CH3:14])[CH2:3][NH:4][C:5](=[O:13])[C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[N:8][CH:7]=1.[CH3:16][N:17]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:18](Cl)=[O:19].N12CCN(CC1)CC2>O1CCCC1>[CH3:1][C:2]([CH3:15])([CH3:14])[CH2:3][NH:4][C:5]([C:6]1[CH:11]=[CH:10][C:9]([O:12][C:18](=[O:19])[N:17]([CH3:16])[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[N:8][CH:7]=1)=[O:13]

Participants

5

Reactant 3

HCID 9237DabcoHCID 77969Carbamic chloride, N-methyl-N-phenyl-HCID 178446492HCID 178446492, compound

Product 1

HCID 69518341Carbamic acid, methylphenyl-, 5-[[(2,2-dimethylpropyl)amino]carbonyl]-2-pyridinyl esterYield 52.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of N-(2,2-dimethyl-propyl)-6-hydroxy-nicotinamide (0.50 g, 2.40 mmol), N-methyl-N-phenylcarbamoyl chloride (0.41 g, 2.40 mmol) and 1,4-diazabicyclo[2,2,2]octane (0.27 g, 2.40 mmol) in tetrahydrofuran (15 mL) was stirred at room temperature for 3 hours. The solvent was evaporated in vacuo and the residue was purified by flash column chromatography (first column: SiO2, dichloromethane:ethyl acetate 95:5, second column: SiO2, ethyl acetate), yielding the title compound (0.43 g, 52% yield).

Workup

  1. customThe solvent was evaporated in vacuo
  2. customthe residue was purified by flash column chromatography (first column: SiO2, dichloromethane:ethyl acetate 95:5, second column: SiO2, ethyl acetate)

Sources & evidence

ORD record
ord-c0fff6ae15bb4b079528d4e6e65a43e6
Source dataset
uspto-grants-2007_10
Patent number
US07279470B2

Reaction notes

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