Sodium Hydroxide → [6-Cyano-6-(4-methoxydibenzo[b,d]furan-1-yl)-4-oxo-5,6,7,8-tetrahydroquinazolin-3(4H)-yl]acetic acid

HRID 2383987Notes

Reaction equation

HRID 2383987 reaction equation
[C:1]([C:3]1([C:20]2[C:28]3[C:27]4[CH:29]=[CH:30][CH:31]=[CH:32][C:26]=4[O:25][C:24]=3[C:23]([O:33][CH3:34])=[CH:22][CH:21]=2)[CH2:12][CH2:11][C:10]2[N:9]=[CH:8][N:7]([CH2:13][C:14]([O:16]CC)=[O:15])[C:6](=[O:19])[C:5]=2[CH2:4]1)#[N:2].[OH-].[Na+]>C(O)C.O>[C:1]([C:3]1([C:20]2[C:28]3[C:27]4[CH:29]=[CH:30][CH:31]=[CH:32][C:26]=4[O:25][C:24]=3[C:23]([O:33][CH3:34])=[CH:22][CH:21]=2)[CH2:12][CH2:11][C:10]2[N:9]=[CH:8][N:7]([CH2:13][C:14]([OH:16])=[O:15])[C:6](=[O:19])[C:5]=2[CH2:4]1)#[N:2]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 24804607Ethyl [6-cyano-6-(4-methoxydibenzo[b,d]furan-1-yl)-4-oxo-5,6,7,8-tetrahydroquinazolin-3(4H)-yl]acetate

Product 1

HCID 24804608[6-Cyano-6-(4-methoxydibenzo[b,d]furan-1-yl)-4-oxo-5,6,7,8-tetrahydroquinazolin-3(4H)-yl]acetic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a stirred solution of the compound obtained in example 19 (100 mg, 0.2188 mmol) in 4 ml of ethanol was added 1N NaOH solution (3 ml) and the reaction mass was allowed to stir at room temperature for 4 hrs. The reaction mass was diluted with 20 ml water and washed 3 timed with 25 ml diethyl ether. The aqueous layer was acidified with 1N aq. HCl to pH 2-3 and extracted with chloroform. The organic layer was washed with water followed by brine, and concentrated under vacuum. The residue was triturated with ether to give 45 mg (Yields-48%) of product.

Workup

  1. washwashed 3
  2. extractionextracted with chloroform
  3. washThe organic layer was washed with water
  4. concentrationconcentrated under vacuum
  5. customThe residue was triturated with ether
  6. customto give
  7. custom45 mg (Yields-48%) of product

Sources & evidence

ORD record
ord-aca2878fb302459a94ab8e561641bc36
Source dataset
uspto-grants-2012_09
Patent number
US08263648B2

Reaction notes

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