Hydrochloric Acid → 3-[1-(7-Carboxymethyloxy-6-methoxy-4-quinazolinyl)-4-piperidinyl]-1,2,3,4-tetrahydro-1,6-dimethyl-2,4-dioxo-quinazoline

HRID 55051Notes

Reaction equation

HRID 55051 reaction equation
C([O:3][C:4]([CH2:6][O:7][C:8]1[CH:17]=[C:16]2[C:11]([C:12]([N:18]3[CH2:23][CH2:22][CH:21]([N:24]4[C:33](=[O:34])[C:32]5[C:27](=[CH:28][CH:29]=[C:30]([CH3:35])[CH:31]=5)[N:26]([CH3:36])[C:25]4=[O:37])[CH2:20][CH2:19]3)=[N:13][CH:14]=[N:15]2)=[CH:10][C:9]=1[O:38][CH3:39])=[O:5])C.[OH-].[Na+].Cl>CO>[C:4]([CH2:6][O:7][C:8]1[CH:17]=[C:16]2[C:11]([C:12]([N:18]3[CH2:19][CH2:20][CH:21]([N:24]4[C:33](=[O:34])[C:32]5[C:27](=[CH:28][CH:29]=[C:30]([CH3:35])[CH:31]=5)[N:26]([CH3:36])[C:25]4=[O:37])[CH2:22][CH2:23]3)=[N:13][CH:14]=[N:15]2)=[CH:10][C:9]=1[O:38][CH3:39])([OH:5])=[O:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 229234383-[1-(7-Ethoxycarbonylmethoxy-6-methoxy-4-quinazolinyl)-4-piperidinyl]-1,2,3,4-tetrahydro-1,6-dimethyl-2,4-dioxoquinazoline

Product 1

HCID 229234763-[1-(7-Carboxymethyloxy-6-methoxy-4-quinazolinyl)-4-piperidinyl]-1,2,3,4-tetrahydro-1,6-dimethyl-2,4-dioxo-quinazolineYield 33%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In 10 ml of methanol was dissolved 250.0 mg (0.47 mmol) of Compound 93 obtained in Example 84, and 5 ml of a 2N aqueous solution of sodium hydroxide was added thereto, followed by heating under reflux for 6 hours. After cooling, the reaction mixture was neutralized by addition of 4N hydrochloric acid, and extracted with chloroform. The organic layer was washed and dried, and the solvent was distilled off under reduced pressure. To the residue was added ether, and the precipitated crystals were collected by filtration and dried to give 77.8 mg (yield: 33%) of Compound 95 as white crystals.

Workup

  1. additionwas added
  2. temperatureby heating
  3. temperatureunder reflux for 6 hours
  4. temperatureAfter cooling
  5. extractionextracted with chloroform
  6. washThe organic layer was washed
  7. customdried
  8. distillationthe solvent was distilled off under reduced pressure
  9. additionTo the residue was added ether
  10. filtrationthe precipitated crystals were collected by filtration
  11. customdried

Sources & evidence

ORD record
ord-859b81e30cc24fbb8f40579742bb0c79
Source dataset
uspto-grants-1997_04
Patent number
US05624926

Reaction notes

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