Dimethyl Sulfoxide → 1-ethyl-6-acetamido-N-(cyclohexylmethyl)-1H-pyrazolo[3,4-b]quinolin-4-amine

HRID 375880Notes

Reaction equation

[CH2:1]([N:3]1[C:7]2=[N:8][C:9]3[C:14]([C:15](Cl)=[C:6]2[CH:5]=[N:4]1)=[CH:13][C:12]([NH:17][C:18](=[O:20])[CH3:19])=[CH:11][CH:10]=3)[CH3:2].[CH:21]1([CH2:27][NH2:28])[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1.CS(C)=O>O>[CH2:1]([N:3]1[C:7]2=[N:8][C:9]3[C:14]([C:15]([NH:28][CH2:27][CH:21]4[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]4)=[C:6]2[CH:5]=[N:4]1)=[CH:13][C:12]([NH:17][C:18](=[O:20])[CH3:19])=[CH:11][CH:10]=3)[CH3:2]

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of 1-ethyl-4-chloro-6-acetamido-1H-pyrazolo[3,4-b]quinoline (0.2 g, 0.7 mmol), cyclohexanemethylamine (0.5 ml, 3.5 mmol) and DMSO (3 ml) was heated at 110° C. for 6 hours. The reaction mixture was poured into water (50 ml), extracted with CH2Cl2 (4×25 ml) and the organic layers were combined and evaporated. The residue was slurried in ether and a yellow solid was collected by filtration and recrystallized from ethanol/ethyl acetate to afford 200 mg of 1-ethyl-6-acetamido-N-(cyclohexylmethyl)-1H-pyrazolo[3,4-b]quinolin-4-amine, m.p. 277°-278° C.

Workup

extractionextracted with CH2Cl2 (4×25 ml)
customevaporated
filtrationa yellow solid was collected by filtration
customrecrystallized from ethanol/ethyl acetate

Sources & evidence

ORD record: ord-3facf5c02f58461fb5b55fc48b8b9854
Source dataset: uspto-grants-1996_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05488055

Reaction notes

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