4-{[(1R)-1-(3-nitrophenyl)ethyl]amino}quinazoline-8-carboxamide → 4-{[(1R)-1-(3-aminophenyl)ethyl]amino}quinazoline-8-carboxamide

HRID 474418Notes

Reaction equation

HRID 474418 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C@H:10]([NH:12][C:13]2[C:22]3[C:17](=[C:18]([C:23]([NH2:25])=[O:24])[CH:19]=[CH:20][CH:21]=3)[N:16]=[CH:15][N:14]=2)[CH3:11])[CH:7]=[CH:8][CH:9]=1)([O-])=O.[H][H]>CO.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]([C@H:10]([NH:12][C:13]2[C:22]3[C:17](=[C:18]([C:23]([NH2:25])=[O:24])[CH:19]=[CH:20][CH:21]=3)[N:16]=[CH:15][N:14]=2)[CH3:11])[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 667629844-{[(1R)-1-(3-nitrophenyl)ethyl]amino}quinazoline-8-carboxamideHCID 178418361HCID 178418361, compound

Product 1

HCID 667628924-{[(1R)-1-(3-aminophenyl)ethyl]amino}quinazoline-8-carboxamideYield 93%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A suspension of 4-{[(1R)-1-(3-nitrophenyl)ethyl]amino}quinazoline-8-carboxamide (1.50 g, 4.45 mmol) in methanol (125 mL) was shaken for 3 h in a Parr vessel under 35 psi hydrogen pressure in the presence of 30 wt % palladium on carbon (600 mg). The material was filtered through Celite, concentrated to get the title compound in 93% yield.

Workup

  1. filtrationThe material was filtered through Celite
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-6ca5de5118e649ec82ce964a5db94f01
Source dataset
uspto-grants-2014_01
Patent number
US08637532B2

Reaction notes

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