Potassium Hydroxide → HCID 21217720, compound

HRID 375888Notes

Reaction equation

HRID 375888 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) was stirred at room temperature overnight. The reaction mixture was partitioned between CH2Cl2 and water and the CH2Cl2 layer was separated and evaporated. The residue was purified by column chromatography on silica gel eluting with 10% ethanol/ethyl acetate to afford the product as the free base. The free base was 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 was partitioned between CH2Cl2 and water
  2. customthe CH2Cl2 layer was separated
  3. customevaporated
  4. customThe residue was 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 was recrystallized from hot ethyl acetate/hexane

Sources & evidence

ORD record
ord-d3638bbc55b745ccb6b7a0dd6b192dee
Source dataset
uspto-grants-1996_01
Patent number
US05488055

Reaction notes

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