Potassium Hydroxide → HCID 21217720, compound

HRID 1586172Notes

Reaction equation

HRID 1586172 reaction equation
Cl.Cl[CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1.[CH2:11]([N:13]1[C:17]2=[N:18][C:19]3[C:24]([C:25]([NH:26][CH2:27][CH:28]4[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]4)=[C:16]2[CH:15]=[N:14]1)=[CH:23][C:22]([OH:34])=[CH:21][CH:20]=3)[CH3:12].[OH-].[K+]>CS(C)=O>[CH2:11]([N:13]1[C:17]2=[N:18][C:19]3[C:24]([C:25]([NH:26][CH2:27][CH:28]4[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]4)=[C:16]2[CH:15]=[N:14]1)=[CH:23][C:22]([O:34][CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1)=[CH:21][CH:20]=3)[CH3:12]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 77210Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1)HCID 9818690HCID 9818690, compound

Product 1

HCID 21217720HCID 21217720, compoundYield 14.7%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of DMSO (6 ml), chloroethylmorpholine hydrochloride (1.23 g, 6.6 mmol), 1-ethyl-6-hydroxy-N-(cyclohexylmethyl)-1H-pyrazolo[3,4-b]quinolin-4-amine (2 g, 6.6 mmol) and KOH (1 g) is stirred at room temperature overnight. The reaction mixture is partitioned between CH2Cl2 and water and the CH2Cl2 layer is separated and evaporated. The residue is purified by column chromatography on silica gel eluting with 10% ethanol/ethyl acetate to afford the product as the free base. The free base is recrystallized from hot ethyl acetate/hexane to afford 0.425 g of 1-ethyl-6-[2-(4-morpholinyl)ethoxy]-N-(cyclohexylmethyl)-1H-pyrazolo[3,4-b]quinolin-4-amine, as a yellow powder, m.p. 176°-178° C.

Workup

  1. customThe reaction mixture is partitioned between CH2Cl2 and water
  2. customthe CH2Cl2 layer is separated
  3. customevaporated
  4. customThe residue is purified by column chromatography on silica gel eluting with 10% ethanol/ethyl acetate
  5. customto afford the product as the free base
  6. customThe free base is recrystallized from hot ethyl acetate/hexane

Sources & evidence

ORD record
ord-b457b5ccff784dac80b3574ee8ca33fb
Source dataset
uspto-grants-1999_08
Patent number
US05942520

Reaction notes

Loading…