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

HRID 1586133Notes

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) is heated at 80° C. overnight. The reaction mixture is pured into water (100 ml)/NH4OH (0.5 ml) and is extracted with CH2Cl2. The solvent is evaporated to about 20 ml and then the mixture is 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 is dissolved in CH2Cl2 (20 ml) and treated with ethereal HCl and the solution is evaporated. The residue is 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

extractionis extracted with CH2Cl2
customThe solvent is evaporated to about 20 ml
customthe mixture is 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 is evaporated
customThe residue is crystallized from ethyl acetate/ether/ethanol

Sources & evidence

ORD record: ord-138438d11554483abc57e245b8c138f7
Source dataset: uspto-grants-1999_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05942520

Reaction notes

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