HCID 67244445, compound → HCID 67246731, compound

HRID 2422639Notes

Reaction equation

HRID 2422639 reaction equation
[CH3:1][N:2]1[C:11](=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([N+:13]([O-])=O)[CH:9]=2)[N:4]=[C:3]1[C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH2:23][CH2:24][CH2:25][N:26]2[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]2)[CH:17]=1.[H][H]>CO.[C].[Pd]>[NH2:13][C:8]1[CH:9]=[C:10]2[C:5](=[CH:6][CH:7]=1)[N:4]=[C:3]([C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH2:23][CH2:24][CH2:25][N:26]3[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31]3)[CH:17]=1)[N:2]([CH3:1])[C:11]2=[O:12]

Participants

5

Reactant 2

HCID 67244445HCID 67244445, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67246731HCID 67246731, compoundYield 44%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

3-Methyl-6-nitro-2-[3-(3-piperidin-1-ylpropoxy)phenyl]-4(3H)-quinazolinone (105 mg, 0.248 mmol) was dissolved in methanol (3 mL), and 10% palladium-carbon (26.4 mg, 0.0248 mmol) was added thereto and stirred in a hydrogen atmosphere at room temperature for 4 days. The reaction solution was filtered through Celite, the Celite was washed with ethyl acetate, and the mother liquid was concentrated. The residue was purified through silica gel column chromatography (chloroform/methanol=3/1) to obtain the intended compound (42.8 mg, 44%) as a yellow solid.

Workup

  1. filtrationThe reaction solution was filtered through Celite
  2. washthe Celite was washed with ethyl acetate
  3. concentrationthe mother liquid was concentrated
  4. customThe residue was purified through silica gel column chromatography (chloroform/methanol=3/1)

Sources & evidence

ORD record
ord-7c1dac1217ae4d6ab145fad663a15c96
Source dataset
uspto-grants-2011_06
Patent number
US07960394B2

Reaction notes

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