Hydrochloric Acid → 1-ethyl-3-methyl-N-(cyclohexylmethyl)-1H-pyrazolo[3,4-b]quinolin-4-amine hydrochloride

HRID 375849Notes

Reaction equation

[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]2[N:12]([CH2:16][CH3:17])[N:13]=[C:14]([CH3:15])[C:3]=12.[CH:18]1([CH2:24][NH2:25])[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1.[NH4+].[OH-].Cl>C(Cl)Cl.O.CS(C)=O>[ClH:1].[CH2:16]([N:12]1[C:4]2=[N:5][C:6]3[C:11]([C:2]([NH:25][CH2:24][CH:18]4[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]4)=[C:3]2[C:14]([CH3:15])=[N:13]1)=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH3:17]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 4-chloro-1-ethyl-3-methyl-1H-pyrazolo[3,4-b]quinoline (1.0 g, 0.0043 mmol), cyclohexanemethylamine (1.2 ml, 0.009 mol) and DMSO (3 ml) was heated at 80° C. overnight. The reaction mixture was pured into water (100 ml)/NH4OH (0.5 ml) and was extracted with CH2Cl2. The solvent was evaporated to about 20 ml and then the mixture was purified by chromatography on silica gel, followed by high pressure liquid chromatography eluting with 20% EtOAc/hexane to 50% EtOAc/hexane to afford the product as the free base. The free base was dissolved in CH2Cl2 (20 ml) and treated with ethereal HCl and the solution was evaporated. The residue was crystallized from ethyl acetate/ether/ethanol to afford 1-ethyl-3-methyl-N-(cyclohexylmethyl)-1H-pyrazolo[3,4-b]quinolin-4-amine hydrochloride, m.p. 215°-217° C.

Workup

extractionwas extracted with CH2Cl2
customThe solvent was evaporated to about 20 ml
customthe mixture was purified by chromatography on silica gel
washeluting with 20% EtOAc/hexane to 50% EtOAc/hexane
customto afford the product as the free base
customthe solution was evaporated
customThe residue was crystallized from ethyl acetate/ether/ethanol

Sources & evidence

ORD record: ord-fe67965e050e43a6b0878baca7d229e6
Source dataset: uspto-grants-1996_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05488055

Reaction notes

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