HCID 131718082, compound → HCID 131718081, compound

HRID 2255094Notes

Reaction equation

HRID 2255094 reaction equation
[CH2:1]([C:5]1[N:14]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])=[CH:18][CH:17]=2)[C:13](=[O:35])[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([N+:36]([O-])=O)[CH:11]=2)[N:6]=1)[CH2:2][CH2:3][CH3:4].[H][H]>CO.[Pd]>[NH2:36][C:10]1[CH:11]=[C:12]2[C:7](=[CH:8][CH:9]=1)[N:6]=[C:5]([CH2:1][CH2:2][CH2:3][CH3:4])[N:14]([CH2:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])=[CH:18][CH:17]=1)[C:13]2=[O:35]

Participants

5

Reactant 2

HCID 131718082HCID 131718082, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 131718081HCID 131718081, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

0.11 g (0.21 mmol) of 2-butyl-3-[(2'-(t-butoxycarbonyl)biphen-4-yl)methyl]-6-nitroquinazolin-3(1H)-one (Example 27) was suspended in 7.5 mL of MeOH and hydrogenated over 55 mg of 10% Pd/C under an atmospheric pressure hydrogen blanket. After 1 hour the reaction mixture was filtered through celite and the filtrate concentrated in vacuo. The residue was purified by flash chromatography over silica gel eluting with 50% EtOAc/hexane to give a white foam. 1H-NMR (CDCl3): 0.94 (t, 3H, J=7. Hz), 1.23 (s, 9H), 1.41 (m, 2H), 1.79 (m, 2H), 2.74 (3 line m, 2H, J=7.7 Hz), 5.44 (bs, 2H), 7.05-7.57 (m, 10H), 7.77 (d, J=7.5 Hz).

Workup

  1. filtrationAfter 1 hour the reaction mixture was filtered through celite
  2. concentrationthe filtrate concentrated in vacuo
  3. customThe residue was purified by flash chromatography over silica gel eluting with 50% EtOAc/hexane
  4. customto give a white foam

Sources & evidence

ORD record
ord-a22041ffa6204258b51cd993bb7d5524
Source dataset
uspto-grants-1993_08
Patent number
US05238942

Reaction notes

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