3-(4,4'-dimethoxybenzhydryl)-2-propyl-6-nitroquinazolin-4(3H)-one → HCID 19934842, compound

HRID 37230Notes

Reaction equation

HRID 37230 reaction equation
[CH3:1][O:2][C:3]1[CH:34]=[CH:33][C:6]([CH:7]([N:16]2[C:25](=[O:26])[C:24]3[C:19](=[CH:20][CH:21]=[C:22]([N+:27]([O-])=O)[CH:23]=3)[N:18]=[C:17]2[CH2:30][CH2:31][CH3:32])[C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=2)=[CH:5][CH:4]=1>CCOC(C)=O.[Pd]>[NH2:27][C:22]1[CH:23]=[C:24]2[C:19](=[CH:20][CH:21]=1)[N:18]=[C:17]([CH2:30][CH2:31][CH3:32])[N:16]([CH:7]([C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:34][CH:33]=1)[C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=1)[C:25]2=[O:26]

Participants

4

Reactant 1

HCID 200766253-(4,4'-dimethoxybenzhydryl)-2-propyl-6-nitroquinazolin-4(3H)-one

Product 1

HCID 19934842HCID 19934842, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 12.1 g (26.0 mmol) of the product of Step B dissolved in 250 mL of EtOAc was hydrogenated under atmospheric pressure over three days in the presence of three portions of 1.2 g of 10% Pd/C added daily. The mixture was filtered through celite and concentrated in vacuo to give an oil. The product was purified by flash chromatography over silica gel eluted with 50% EtOAc/hexanes to give 7.8 g (72%) of the amine.

Workup

  1. additionadded daily
  2. filtrationThe mixture was filtered through celite and
  3. concentrationconcentrated in vacuo
  4. customto give an oil
  5. customThe product was purified by flash chromatography over silica gel
  6. washeluted with 50% EtOAc/hexanes

Sources & evidence

ORD record
ord-181d3e7bd3554d46b1b562f2d487dee5
Source dataset
uspto-grants-1995_05
Patent number
US05420133

Reaction notes

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