4-(Aminomethyl)cyclohexan-1-ol → 1-ethyl-6-methoxy-N-(4-hydroxycyclohexylmethyl)-1H-pyrazolo[3,4-b]quinolin-4-amine

HRID 1586165Notes

Reaction equation

HRID 1586165 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]([O:17][CH3:18])=[CH:11][CH:10]=3)[CH3:2].[OH:19][CH:20]1[CH2:25][CH2:24][CH:23]([CH2:26][NH2:27])[CH2:22][CH2:21]1>CS(C)=O>[CH2:1]([N:3]1[C:7]2=[N:8][C:9]3[C:14]([C:15]([NH:27][CH2:26][CH:23]4[CH2:24][CH2:25][CH:20]([OH:19])[CH2:21][CH2:22]4)=[C:6]2[CH:5]=[N:4]1)=[CH:13][C:12]([O:17][CH3:18])=[CH:11][CH:10]=3)[CH3:2]

Participants

4

Reactant 2

HCID 148675294-(Aminomethyl)cyclohexan-1-olHCID 195922121-ethyl-4-chloro-6-methoxy-1H-pyrazolo[3,4-b]quinoline

Product 1

HCID 98415311-ethyl-6-methoxy-N-(4-hydroxycyclohexylmethyl)-1H-pyrazolo[3,4-b]quinolin-4-amineYield 32.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 1-ethyl-4-chloro-6-methoxy-1H-pyrazolo[3,4-b]quinoline (2.02 g, 15.5 mmol), DMSO (6 ml) and 4-hydroxy cyclohexylmethylamine (2 g, 15.5 mmol) is heated at 110° C. overnight. The reaction mixture is partitioned between CH2Cl2 /water/NaHCO3, and the CH2Cl2 layer is separated, dried over MgSO4 and evaporated. The residue is purified by column chromatography on silica gel eluting with ethyl acetate to afford 1.8 g of 1-ethyl-6-methoxy-N-(4-hydroxycyclohexylmethyl)-1H-pyrazolo[3,4-b]quinolin-4-amine.

Workup

  1. customThe reaction mixture is partitioned between CH2Cl2 /water/NaHCO3
  2. customthe CH2Cl2 layer is separated
  3. dry with materialdried over MgSO4
  4. customevaporated
  5. customThe residue is purified by column chromatography on silica gel eluting with ethyl acetate

Sources & evidence

ORD record
ord-f3c02899ad1f42df9853007c012b4adc
Source dataset
uspto-grants-1999_08
Patent number
US05942520

Reaction notes

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