Sodium hydride → HCID 68832554, compound

HRID 1986471Notes

Reaction equation

HRID 1986471 reaction equation
[H-].[Na+].[Br-].[CH3:4][S+](C)(C)=O.[C:9]([O:13][C:14]([NH:16][CH2:17][C:18]1[C:19]([CH2:42][CH2:43][CH3:44])=[N:20][C:21]2[C:26]([C:27]=1[C:28]1[CH:33]=[CH:32][C:31]([CH3:34])=[CH:30][CH:29]=1)=[CH:25][C:24](/[CH:35]=[CH:36]/[C:37]([O:39][CH2:40][CH3:41])=[O:38])=[CH:23][CH:22]=2)=[O:15])([CH3:12])([CH3:11])[CH3:10].[Cl-].[NH4+]>CS(C)=O>[C:9]([O:13][C:14]([NH:16][CH2:17][C:18]1[C:19]([CH2:42][CH2:43][CH3:44])=[N:20][C:21]2[C:26]([C:27]=1[C:28]1[CH:29]=[CH:30][C:31]([CH3:34])=[CH:32][CH:33]=1)=[CH:25][C:24]([CH:35]1[CH2:4][CH:36]1[C:37]([O:39][CH2:40][CH3:41])=[O:38])=[CH:23][CH:22]=2)=[O:15])([CH3:12])([CH3:11])[CH3:10]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 11126750Trimethylsulfoxonium BromideHCID 86605646HCID 86605646, compound

Product 1

HCID 68832554HCID 68832554, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a suspension of sodium hydride (60% in oil, 120 mg, 3 mmol) in dimethyl sulfoxide (10 ml) was added trimethylsulfoxonium bromide (605 mg, 3.5 mmol), and the mixture was stirred at room temperature for 30 min. To the reaction mixture was added ethyl (2E)-3-[3-{[(tert-butoxycarbonyl)amino]methyl}-4-(4-methylphenyl)-2-propylquinolin-6-yl]acrylate (0.73 g, 1.5 mmol) and the mixture was stirred at room temperature for 1 hr. Saturated aqueous ammonium chloride solution was poured into the reaction mixture and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was crystallized from diisopropyl ether to give ethyl 2-[3-{[(tert-butoxycarbonyl)amino]methyl}-4-(4-methylphenyl)-2-propylquinolin-6-yl]cyclopropane-1-carboxylate (0.61 g, yield 81%) as white crystals.

Workup

  1. stirringthe mixture was stirred at room temperature for 1 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was crystallized from diisopropyl ether

Sources & evidence

ORD record
ord-059044ead9144f19b5a793ddbcd314f7
Source dataset
uspto-grants-2009_06
Patent number
US07547710B2

Reaction notes

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