HCID 22648055, compound → 7-amino-5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-3-(4-methoxybenzyl)-3,4-dihydroquinazolin-2(1H)-one

HRID 394191Notes

Reaction equation

HRID 394191 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:17]=[C:16]([N+:18]([O-])=O)[CH:15]=[C:14]2[C:9]=1[CH2:10][N:11]([CH2:30][C:31]1[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[CH:33][CH:32]=1)[C:12](=[O:29])[N:13]2[C:21]1[C:26]([Cl:27])=[CH:25][CH:24]=[CH:23][C:22]=1[Cl:28]>C(OCC)(=O)C.[Pd]>[NH2:18][C:16]1[CH:15]=[C:14]2[C:9]([CH2:10][N:11]([CH2:30][C:31]3[CH:32]=[CH:33][C:34]([O:37][CH3:38])=[CH:35][CH:36]=3)[C:12](=[O:29])[N:13]2[C:21]2[C:26]([Cl:27])=[CH:25][CH:24]=[CH:23][C:22]=2[Cl:28])=[C:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Cl:1])[CH:17]=1

Participants

4

Reactant 1

HCID 22648055HCID 22648055, compound

Product 1

HCID 226480157-amino-5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-3-(4-methoxybenzyl)-3,4-dihydroquinazolin-2(1H)-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-3-(4-methoxybenzyl)-7-nitro-3,4-dihydroquinazolin-2(1H)-one (20.0 mg, 0.035 mmol) in ethyl acetate (2 mL) was added 10% Pd/C (14.5 mg) under argon. Hydrogen was bubbled through and the reaction mixture was stirred under hydrogen for 1.5 h. The reaction flask was purged with argon. The catalyst was filtered off washing with methanol. The filtrate was concentrated under reduced pressure to yield 7-amino-5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-3-(4-methoxybenzyl)-3,4-dihydroquinazolin-2(1H)-one. Mass spectrum (ESI) 538.2 (M+1).

Workup

  1. customHydrogen was bubbled through and the reaction mixture
  2. customThe reaction flask was purged with argon
  3. filtrationThe catalyst was filtered off
  4. washwashing with methanol
  5. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-24019290c15a4b149a4c025ae146158f
Source dataset
uspto-grants-2004_10
Patent number
US06809199B2

Reaction notes

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