8-Nitro-2-(4-phenoxyphenyl)-4,5-dihydropyrazolo[1,5-a]quinazoline-3-carboxamide → 8-Amino-2-(4-phenoxyphenyl)-4,5-dihydropyrazolo[1,5-a]quinazoline-3-carboxamide

HRID 64343Notes

Reaction equation

HRID 64343 reaction equation
[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][NH:9][C:10]3[N:11]2[N:14]=[C:15]([C:20]2[CH:25]=[CH:24][C:23]([O:26][C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)=[CH:22][CH:21]=2)[C:16]=3[C:17]([NH2:19])=[O:18])=[CH:6][CH:5]=1)([O-])=O>CO.C(Cl)Cl.[Pd]>[NH2:1][C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][NH:9][C:10]3[N:11]2[N:14]=[C:15]([C:20]2[CH:25]=[CH:24][C:23]([O:26][C:27]4[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=4)=[CH:22][CH:21]=2)[C:16]=3[C:17]([NH2:19])=[O:18])=[CH:6][CH:5]=1

Participants

5

Reactant 1

HCID 1369280608-Nitro-2-(4-phenoxyphenyl)-4,5-dihydropyrazolo[1,5-a]quinazoline-3-carboxamide

Product 1

HCID 1369280938-Amino-2-(4-phenoxyphenyl)-4,5-dihydropyrazolo[1,5-a]quinazoline-3-carboxamideYield 70%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 8-nitro-2-(4-phenoxyphenyl)-4,5-dihydropyrazolo[1,5-a]quinazoline-3-carboxamide (200 mg, 0.47 mmol) in 30 mL of CH3OH and 30 mL of DCM was added 10% w/w Pd/C (100 mg). After stirring at RT for 1 hr, the mixture was filtered. The filtrate was concentrated to afford 130 mg (70%) of crude 8-amino-2-(4-phenoxyphenyl)-4,5-dihydropyrazolo[1,5-a]quinazoline-3-carboxamide and 8-amino-2-(4-phenoxyphenyl)pyrazolo[1,5-a]quinazoline-3-carboxamide as a yellow solid. MS (ESI) m/e [M+1]+398.0, 395.9.

Workup

  1. filtrationthe mixture was filtered
  2. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-ee345e2ffdb8461e8ff2ce3e28972f29
Source dataset
uspto-grants-2016_09
Patent number
US09447106B2

Reaction notes

Loading…