Ammonium Chloride → 8-[(4-amino-2-methoxyphenyl)amino]-N-(2,6-diethylphenyl)-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide

HRID 81968Notes

Reaction equation

[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][CH3:10])[C:4]=1[NH:11][C:12]([C:14]1[C:18]2[CH2:19][CH2:20][C:21]3[CH:22]=[N:23][C:24]([NH:27][C:28]4[CH:33]=[CH:32][C:31]([N+:34]([O-])=O)=[CH:30][C:29]=4[O:37][CH3:38])=[N:25][C:26]=3[C:17]=2[N:16]([CH3:39])[N:15]=1)=[O:13])[CH3:2].[Cl-].[NH4+]>O1CCOCC1.O.[Zn]>[NH2:34][C:31]1[CH:32]=[CH:33][C:28]([NH:27][C:24]2[N:23]=[CH:22][C:21]3[CH2:20][CH2:19][C:18]4[C:14]([C:12]([NH:11][C:4]5[C:5]([CH2:9][CH3:10])=[CH:6][CH:7]=[CH:8][C:3]=5[CH2:1][CH3:2])=[O:13])=[N:15][N:16]([CH3:39])[C:17]=4[C:26]=3[N:25]=2)=[C:29]([O:37][CH3:38])[CH:30]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a suspension of N-(2,6-diethylphenyl)-8-[(2-methoxy-4-nitrophenyl)amino]-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide (1.4 g, 2.656 mmol) in 27 ml of dioxane, zinc (695 mg, 10.624 mmol) and ammonium chloride (1.4 g, 26.56 mmol) in 2.7 ml of water were added and heated at 100° C. under stirring for 8 h. The mixture was cooled, the insoluble material filtered off and washed with ethyl acetate, the combined organic solutions are washed with aqueous citric acid solution, dried on Na2SO4 and evaporated in vacuo leaving a pink foam as crude title product that has been used without any further purification.

Workup

additionwere added
temperatureThe mixture was cooled
filtrationthe insoluble material filtered off
washwashed with ethyl acetate
washthe combined organic solutions are washed with aqueous citric acid solution
customdried on Na2SO4
customevaporated in vacuo

Sources & evidence

ORD record: ord-e7ebc8c27ae24857a92884a9923a535a
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846701B2

Reaction notes

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