HCID 54544936, compound → HCID 18362995, compound

HRID 381274Notes

Reaction equation

HRID 381274 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:17](=[O:18])[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([F:19])[CH:15]=2)[N:10]=[C:9]1[CH:20]=[CH:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=1.[H][H]>C(OCC)(=O)C.[Pd]>[ClH:1].[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:17](=[O:18])[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([F:19])[CH:15]=2)[N:10]=[C:9]1[CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=1

Participants

5

Reactant 2

HCID 54544936HCID 54544936, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 18362995HCID 18362995, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1.00 gram (2.65 mmol) of 3-(2-Chloro-phenyl)-6-fluoro-2-(2-pyridin-2-yl-vinyl)-3H-quinazolin-4-one in about 100 mL of ethyl acetate was treated with 0.5 gram of 10% Pd/C and the resulting mixture was hydrogenated at about 2 cm of Hg for two hours at which time uptake of hydrogen had ceased. The catalyst was filtered off with the aid of supercel (filteraid) and the ethyl acetate was removed by evaporation. The residues were dissolved in diethyl ether and treated with excess of a solution of HCl gas in diethyl ether. The product precipitated immediately and was allowed to stir for 3 hours at which time it was separated by filtration and dried in a stream of dry nitrogen. The product was 1.15 g (100%) of 3-(2-chloro-phenyl)-6-fluoro-2-(2-pyridin-2-yl-ethyl)-3H-quinazolin-4-one hydrochloride, an amorphous white solid.

Workup

  1. filtrationThe catalyst was filtered off with the aid of supercel (filteraid)
  2. customthe ethyl acetate was removed by evaporation
  3. dissolutionThe residues were dissolved in diethyl ether
  4. additiontreated with excess of a solution of HCl gas in diethyl ether
  5. customThe product precipitated immediately
  6. customwas separated by filtration
  7. customdried in a stream of dry nitrogen

Sources & evidence

ORD record
ord-be68ff40883f426a8b416c4916743d6b
Source dataset
uspto-grants-2001_10
Patent number
US06306864B1

Reaction notes

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