Sodium borohydride → HCID 21108201, compound

HRID 1766019Notes

Reaction equation

HRID 1766019 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([N:18]3[C:27]4[C:22](=[CH:23][C:24]([C:28](=[O:34])/[CH:29]=[CH:30]/[N:31]([CH3:33])[CH3:32])=[CH:25][CH:26]=4)[CH2:21][CH2:20][CH2:19]3)=[O:17])=[CH:12][CH:11]=2)=[CH:6][CH:5]=1>CO>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([N:18]3[C:27]4[C:22](=[CH:23][C:24]([CH:28]([OH:34])[CH2:29][CH2:30][N:31]([CH3:33])[CH3:32])=[CH:25][CH:26]=4)[CH2:21][CH2:20][CH2:19]3)=[O:17])=[CH:12][CH:11]=2)=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 21108378HCID 21108378, compound

Product 1

HCID 21108201HCID 21108201, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (0.6 g) was added to a solution of (E)-[1-[(4′-chloro[1,1′-biphenyl]-4-yl)carbonyl]-1,2,3,4-tetrahydro-6-quinolinyl]-3-(dimethylamino)-2-propen-1-one (0.3 g) obtained in Reference Example 6 in methanol (30 ml), and the mixture was heated for 3 hours under reflux. After the solvent was distilled away under reduced pressure, the residues were dissolved in water-ethyl acetate and extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate, and the solvent was distilled away under reduced pressure. The resultant residues were purified by alumina column chromatography (developing solvent; ethyl acetate), whereby the title compound (0.1 g) was obtained as amorphous powder.

Workup

  1. temperaturethe mixture was heated for 3 hours
  2. temperatureunder reflux
  3. distillationAfter the solvent was distilled away under reduced pressure
  4. dissolutionthe residues were dissolved in water-ethyl acetate
  5. extractionextracted with ethyl acetate
  6. washThe extract was washed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationthe solvent was distilled away under reduced pressure
  9. customThe resultant residues were purified by alumina column chromatography (developing solvent; ethyl acetate), whereby the title compound (0.1 g)
  10. customwas obtained as amorphous powder

Sources & evidence

ORD record
ord-8bdd15f9cc8b4e9580d2ebe13a4ca743
Source dataset
uspto-grants-2007_06
Patent number
US07229986B2

Reaction notes

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