Triethylamine → HCID 68829607, compound

HRID 1986460Notes

Reaction equation

HRID 1986460 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[N:15]=[C:14]([CH2:19][CH:20]([CH3:22])[CH3:21])[C:13]([CH2:23]O)=[C:12]2[CH2:25][CH2:26][CH2:27][CH3:28])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.CS(Cl)(=O)=O.[C:41]1(=[O:51])[NH:45][C:44](=[O:46])[C:43]2=[CH:47][CH:48]=[CH:49][CH:50]=[C:42]12.[K]>O1CCCC1.O>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[N:15]=[C:14]([CH2:19][CH:20]([CH3:22])[CH3:21])[C:13]([CH2:23][N:45]1[C:41](=[O:51])[C:42]3[C:43](=[CH:47][CH:48]=[CH:49][CH:50]=3)[C:44]1=[O:46])=[C:12]2[CH2:25][CH2:26][CH2:27][CH3:28])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 24194345Phthalimide potassium saltHCID 68830301HCID 68830301, compound

Product 1

HCID 68829607HCID 68829607, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of [6-(benzyloxy)-4-butyl-2-isobutylquinolin-3-yl]methanol (1.43 g, 3.8 mmol) in tetrahydrofuran (20 ml) were added triethylamine (0.64 ml, 4.6 mmol) and methanesulfonyl chloride (0.36 ml, 4.6 mmol) and the mixture was stirred at 0° C. for 1 hr. The reaction mixture was poured into water and extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was dissolved in N,N-dimethylformamide (30 ml). Potassium phthalimide (1.41 g, 7.6 mmol) was added, and the mixture was stirred at room temperature for 6 hrs. The reaction mixture was poured into water and extracted with ethyl acetate. The extract was washed with 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 2-{[6-(benzyloxy)-4-butyl-2-isobutylquinolin-3-yl]methyl}-1H-isoindole-1,3(2H)-dione (1.81 g, yield 94%) as white crystals.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract 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 N,N-dimethylformamide (30 ml)
  6. stirringthe mixture was stirred at room temperature for 6 hrs
  7. extractionextracted with ethyl acetate
  8. washThe extract was washed with saturated brine
  9. dry with materialdried over anhydrous magnesium sulfate
  10. customThe solvent was evaporated under reduced pressure
  11. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-67f14eb2269046a0b90f5e27efd854f4
Source dataset
uspto-grants-2009_06
Patent number
US07547710B2

Reaction notes

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