Hydrochloric Acid → 6-Carboxy-3-[1-(6,7-dimethoxy-4-quinazolinyl)-4-piperidinyl]-1,2,3,4-tetrahydro-1-methyl-2,4-dioxo-quinazoline

HRID 55055Notes

Reaction equation

HRID 55055 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]([CH3:14])[C:9](=[O:15])[N:8]([CH:16]1[CH2:21][CH2:20][N:19]([C:22]3[C:31]4[C:26](=[CH:27][C:28]([O:34][CH3:35])=[C:29]([O:32][CH3:33])[CH:30]=4)[N:25]=[CH:24][N:23]=3)[CH2:18][CH2:17]1)[C:7]2=[O:36])(=[O:3])C.Br[OH:38].BrBr.[OH-].[Na+].Cl>O1CCOCC1.C(Cl)(Cl)Cl>[C:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]([CH3:14])[C:9](=[O:15])[N:8]([CH:16]1[CH2:17][CH2:18][N:19]([C:22]3[C:31]4[C:26](=[CH:27][C:28]([O:34][CH3:35])=[C:29]([O:32][CH3:33])[CH:30]=4)[N:25]=[CH:24][N:23]=3)[CH2:20][CH2:21]1)[C:7]2=[O:36])([OH:3])=[O:38]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 24408BromineHCID 83547Hypobromous acidHCID 229233736-Acetyl-3-[1-(6,7-dimethoxy-4-quinazolinyl)-4-piperidinyl]-1,2,3,4-tetrahydro-1-methyl-2,4-dioxo-quinazoline

Product 1

HCID 229233886-Carboxy-3-[1-(6,7-dimethoxy-4-quinazolinyl)-4-piperidinyl]-1,2,3,4-tetrahydro-1-methyl-2,4-dioxo-quinazolineYield 21.3%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 312751,4-DioxaneSolvent2×

Procedure

In a solvent mixture of 30 ml of 1,4-dioxane and 5 ml of chloroform was suspended 245.0 mg (0.50 mmol) of Compound 63 obtained in Example 50. The suspension was added to a solution of hypobromous acid (3 mmol) which was prepared by adding 0.15 ml of bromine to a solvent mixture of 3 ml of a 2N aqueous solution of sodium hydroxide and 1 ml of 1,4-dioxane under ice cooling. The mixture was stirred at room temperature for one day, and then neutralized by addition of 4N hydrochloric acid, followed by extraction 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 52.4 mg (yield: 21%) of Compound 62 as white crystals.

Workup

  1. customwas prepared
  2. extractionfollowed by extraction with chloroform
  3. washThe organic layer was washed
  4. customdried
  5. distillationthe solvent was distilled off under reduced pressure
  6. additionTo the residue was added ether
  7. filtrationthe precipitated crystals were collected by filtration
  8. customdried

Sources & evidence

ORD record
ord-5671186726a84749a382b44035b9f6a9
Source dataset
uspto-grants-1997_04
Patent number
US05624926

Reaction notes

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