Water → HCID 22923376, compound

HRID 1451914Notes

Reaction equation

HRID 1451914 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[C:5]([N:16]2[CH2:21][CH2:20][CH:19]([N:22]3[C:31](=[O:32])[C:30]4[C:25](=[CH:26][CH:27]=[C:28]([CH3:33])[CH:29]=4)[N:24]([CH3:34])[C:23]3=[O:35])[CH2:18][CH2:17]2)=[N:4][N:3]=1.O>C(O)(=O)C.[Pd]>[CH3:13][O:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][C:8]=1[O:14][CH3:15])[C:5]([N:16]1[CH2:17][CH2:18][CH:19]([N:22]3[C:31](=[O:32])[C:30]4[C:25](=[CH:26][CH:27]=[C:28]([CH3:33])[CH:29]=4)[N:24]([CH3:34])[C:23]3=[O:35])[CH2:20][CH2:21]1)=[N:4][N:3]=[CH:2]2

Participants

5

Reactant 2

HCID 962WaterHCID 229234613-[1-(4-Chloro-6,7-dimethoxy-1-phthalazinyl)-4-piperidinyl]-1,2,3,4-tetrahydro-1,6-dimethyl-2,4-dioxo-quinazoline

Product 1

HCID 22923376HCID 22923376, compoundYield 19%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
40 °C

Procedure

In 10 ml of acetic acid was dissolved 300 mg (0.61 mmol) of Compound 76 obtained in Example 58, and 40 mg of 10% palladium on carbon suspended in a small amount of water was added to the solution, followed by vigorous stirring at 40° C. for 3 hours under a hydrogen atmosphere at atmospheric pressure. The reaction mixture was filtered using a filter aid, and the filtrate was neutralized by addition of a saturated aqueous solution of sodium bicarbonate and extracted with ethyl acetate. The organic layer was washed successively with water and a saturated aqueous solution of sodium chloride, and then dried. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: chloroform/methanol=50/1). Ether was added to the product, and the precipitated crystals were collected by filtration, washed, and dried to give 52.9 mg (yield: 19%) of Compound 77 as white crystals.

Workup

  1. additionwas added to the solution
  2. filtrationThe reaction mixture was filtered
  3. additionthe filtrate was neutralized by addition of a saturated aqueous solution of sodium bicarbonate
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed successively with water
  6. dry with materiala saturated aqueous solution of sodium chloride, and then dried
  7. distillationThe solvent was distilled off under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (eluent: chloroform/methanol=50/1)
  9. additionEther was added to the product
  10. filtrationthe precipitated crystals were collected by filtration
  11. washwashed
  12. customdried

Sources & evidence

ORD record
ord-d92f8cd30f18476095717bcc78fad9e8
Source dataset
uspto-grants-1997_02
Patent number
US05605900

Reaction notes

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