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

HRID 64342Notes

Reaction equation

HRID 64342 reaction equation
[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH:8]=[N: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-:3])=[O:2].[BH4-].[Na+].O>CCO.C(Cl)Cl>[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: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)([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 1176683998-Nitro-2-(4-phenoxyphenyl)pyrazolo[1,5-a]quinazoline-3-carboxamide

Product 1

HCID 1369280608-Nitro-2-(4-phenoxyphenyl)-4,5-dihydropyrazolo[1,5-a]quinazoline-3-carboxamideYield 83%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 8-nitro-2-(4-phenoxyphenyl)pyrazolo[1,5-a]quinazoline-3-carboxamide (240 mg, 0.57 mmol) in 10 mL of EtOH and 10 mL of DCM was added NaBH4 (86 mg, 2.26 mmol) at RT. After stirring at RT for 20 min, 10 mL of water was added. The mixture was concentrated. 5 mL of water was added and filtered. The cake was washed with tert-Butyl methyl ether (30 mL) and dried to afford 200 mg (83%) of 8-nitro-2-(4-phenoxyphenyl)-4,5-dihydropyrazolo[1,5-a]quinazoline-3-carboxamide as a yellow solid. MS (ESI) m/e [M+1]+ 427.9.

Workup

  1. concentrationThe mixture was concentrated
  2. addition5 mL of water was added
  3. filtrationfiltered
  4. washThe cake was washed with tert-Butyl methyl ether (30 mL)
  5. customdried

Sources & evidence

ORD record
ord-00dbbd0f5b054c6d8bc13cddf4418442
Source dataset
uspto-grants-2016_09
Patent number
US09447106B2

Reaction notes

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