Ethanol → HCID 22449885, compound

HRID 2187068Notes

Reaction equation

HRID 2187068 reaction equation
C([CH:3]([C:43](N)=[O:44])[C:4]([NH:6][C:7]1[CH:16]=[C:15]2[C:10]([C:11](=[O:42])[NH:12][C:13](=[O:41])[N:14]2[CH2:17][CH2:18][CH2:19][CH2:20][N:21]2[CH2:26][CH2:25][CH:24]([O:27][CH:28]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH2:23][CH2:22]2)=[CH:9][CH:8]=1)=[O:5])C.C([OH:48])C.[OH-].[Na+]>O1CCCC1>[O:41]=[C:13]1[NH:12][C:11](=[O:42])[C:10]2[C:15](=[CH:16][C:7]([NH:6][C:4]([CH2:3][C:43]([OH:48])=[O:44])=[O:5])=[CH:8][CH:9]=2)[N:14]1[CH2:17][CH2:18][CH2:19][CH2:20][N:21]1[CH2:26][CH2:25][CH:24]([O:27][CH:28]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:23][CH2:22]1

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 70154155HCID 70154155, compound

Product 1

HCID 22449885HCID 22449885, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl N-[2,4-dioxo-1-[4-(4-diphenylmethoxypiperidino)butyl]-1,2,3,4-tetrahydro-7-quinazolinyl]malonamide (690 mg) obtained in Example 43 was dissolved in tetrahydrofuran (10.0 ml) and ethanol (10.0 ml) and then a 1N aqueous solution of sodium hydroxide (5.0 ml) was added. The reaction mixture was stirred at room temperature for 16 hours and the solvent was distilled off under reduced pressure, and the residue was made acidic with 1N hydrochloric acid, and then extracted with ethyl acetate. After the extract was washed with water and dried (Na2SO4), the solvent was distilled off under reduced pressure to give the title compound (126 mg, 19%). Recrystallization from ethyl acetate-methanol-tetrahydrofuran yielded a colorless crystal having a melting point of 230 to 232° C.

Workup

  1. distillationthe solvent was distilled off under reduced pressure
  2. extractionextracted with ethyl acetate
  3. washAfter the extract was washed with water
  4. dry with materialdried (Na2SO4)
  5. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-56eedfa83bc6411d8049f1ea14dc0535
Source dataset
uspto-grants-2002_06
Patent number
US06407116B1

Reaction notes

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