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

HRID 375849
Notes
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Reaction equation

HRID 375849 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 14923Ammonium HydroxideHCID 76688CyclohexanemethylamineHCID 195922341-ethyl-3-methyl-4-chloro-1H-pyrazolo[3,4-b]quinoline

Product 1

HCID 212177241-ethyl-3-methyl-N-(cyclohexylmethyl)-1H-pyrazolo[3,4-b]quinolin-4-amine hydrochloride

Reagents, catalysts & solvents 3

HCID 679
Dimethyl Sulfoxide
Solvent
HCID 962WaterSolvent
HCID 6344DichloromethaneSolvent

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

  1. extractionwas extracted with CH2Cl2
  2. customThe solvent was evaporated to about 20 ml
  3. customthe mixture was purified by chromatography on silica gel
  4. washeluting with 20% EtOAc/hexane to 50% EtOAc/hexane
  5. customto afford the product as the free base
  6. customthe solution was evaporated
  7. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes