HCID 117668193, compound → 8-Nitro-2-(4-phenoxyphenyl)pyrazolo[1,5-a]quinazoline-3-carboxamide

HRID 64341Notes

Reaction equation

HRID 64341 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[CH:10]=[CH:9][C:8]=2[CH:16]=O)[N:5]=[C:4]([C:18]2[CH:23]=[CH:22][C:21]([O:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[CH:20][CH:19]=2)[C:3]=1[C:31]([NH2:33])=[O:32]>CO.C(Cl)Cl.CC(O)=O>[N+:13]([C:11]1[CH:12]=[C:7]2[C:8]([CH:16]=[N:1][C:2]3[N:6]2[N:5]=[C:4]([C:18]2[CH:19]=[CH:20][C:21]([O:24][C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=4)=[CH:22][CH:23]=2)[C:3]=3[C:31]([NH2:33])=[O:32])=[CH:9][CH:10]=1)([O-:15])=[O:14]

Participants

5

Reactant 1

HCID 117668193HCID 117668193, compound

Product 1

HCID 1176683998-Nitro-2-(4-phenoxyphenyl)pyrazolo[1,5-a]quinazoline-3-carboxamideYield 63%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-amino-1-(2-formyl-5-nitrophenyl)-3-(4-phenoxyphenyl)-1H-pyrazole-4-carboxamide (400 mg, 0.9 mmol) in 5 mL of CH3OH and 5 mL of DCM was added HOAc (1 drops). After stirring at RT for 16 hr, the mixture was concentrated and purified by chromatography column on silica gel eluting with PE/EA to afford 240 mg (63%) of 8-nitro-2-(4-phenoxyphenyl)pyrazolo[1,5-a]quinazoline-3-carboxamide as a yellow solid. MS (ESI) m/e [M+1]+ 425.8.

Workup

  1. concentrationthe mixture was concentrated
  2. custompurified by chromatography column on silica gel eluting with PE/EA

Sources & evidence

ORD record
ord-941f09702f8d40689a6bee918e35fbaa
Source dataset
uspto-grants-2016_09
Patent number
US09447106B2

Reaction notes

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