Triethylamine → HCID 51050346, compound

HRID 1986506Notes

Reaction equation

HRID 1986506 reaction equation
O[CH2:2][CH2:3][CH2:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[N:11]=[C:10]([CH2:15][CH:16]([CH3:18])[CH3:17])[C:9]([CH2:19][NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[C:8]2[C:28]1[CH:33]=[CH:32][C:31]([CH3:34])=[CH:30][CH:29]=1.C(N(CC)CC)C.CS(Cl)(=O)=O.C(=O)([O-])O.[Na+].[C-:52]#[N:53].[K+]>O1CCCC1.C(OCC)(=O)C>[C:52]([CH2:2][CH2:3][CH2:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[N:11]=[C:10]([CH2:15][CH:16]([CH3:18])[CH3:17])[C:9]([CH2:19][NH:20][C:21](=[O:27])[O:22][C:23]([CH3:25])([CH3:26])[CH3:24])=[C:8]2[C:28]1[CH:29]=[CH:30][C:31]([CH3:34])=[CH:32][CH:33]=1)#[N:53]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 9032Potassium CyanideHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 51050453HCID 51050453, compound

Product 1

HCID 51050346HCID 51050346, compoundYield 89.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl {[6-(3-hydroxypropyl)-2-isobutyl-4-(4-methylphenyl)quinolin-3-yl]methyl}carbamate (3.00 g, 6.48 mmol) and triethylamine (1.8 ml, 12.9 mmol) in tetrahydrofuran (50 ml) was added dropwise methanesulfonyl chloride (1.12 g, 9.73 mmol) at 0° C., and the mixture was stirred at the same temperature for 30 min. Saturated aqueous sodium hydrogen carbonate was added to the reaction mixture and the mixture was extracted twice with ethyl acetate. The combined organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was dissolved in dimethyl sulfoxide (40 ml). Potassium cyanide (2.1 g, 32.4 mmol) was added and the mixture was stirred at 60° C. for 2.5 hrs. The reaction mixture was diluted with ethyl acetate, washed twice with saturated aqueous sodium hydrogen carbonate, water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography to give tert-butyl {[6-(3-cyanopropyl)-2-isobutyl-4-(4-methylphenyl)quinolin-3-yl]methyl}carbamate (2.73 g, yield 89%) as yellow crystals.

Workup

  1. extractionthe mixture was extracted twice with ethyl acetate
  2. washThe combined organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. dissolutionthe residue was dissolved in dimethyl sulfoxide (40 ml)
  6. stirringthe mixture was stirred at 60° C. for 2.5 hrs
  7. washwashed twice with saturated aqueous sodium hydrogen carbonate, water and saturated brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customThe solvent was evaporated under reduced pressure
  10. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-b47fd78fe3d6467892579061e7f6a6cf
Source dataset
uspto-grants-2009_06
Patent number
US07547710B2

Reaction notes

Loading…