Epichlorohydrin → HCID 86749231, compound

HRID 375867Notes

Reaction equation

HRID 375867 reaction equation
[CH2:1]([N:3]1[C:7]2=[N:8][C:9]3[C:14]([C:15]([NH:16][CH2:17][CH:18]4[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]4)=[C:6]2[CH:5]=[N:4]1)=[CH:13][C:12]([OH:24])=[CH:11][CH:10]=3)[CH3:2].[OH-].[K+].[CH2:27]([CH:29]1[O:31][CH2:30]1)Cl>CS(C)=O>[CH2:1]([N:3]1[C:7]2=[N:8][C:9]3[C:14]([C:15]([NH:16][CH2:17][CH:18]4[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]4)=[C:6]2[CH:5]=[N:4]1)=[CH:13][C:12]([O:24][CH2:27][CH:29]1[O:31][CH2:30]1)=[CH:11][CH:10]=3)[CH3:2]

Participants

5

Reactant 3

HCID 7835EpichlorohydrinHCID 14797Potassium HydroxideHCID 9818690HCID 9818690, compound

Product 1

HCID 86749231HCID 86749231, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 1-ethyl-6-hydroxy-N-(cyclohexylmethyl)-1H-pyrazolo[3,4-b]quinolin-4-amine (6 g), KOH (5 g), and DMSO (70 ml) was stirred for 30 minutes and then epichlorohydrin (1.5 ml) was added. The reaction mixture was stirred overnight and then was partitioned between CH2Cl2 and water. The organic layer was then separated, dried and evaporated to dryness. The residue was purified by column chromatography on silica gel eluting with ethyl acetate, followed by crystallization from hexane/ether to afford 1.0 g of 1-ethyl-6-(2,3-epoxypropoxy)-N-(cyclohexylmethyl)-1H-pyrazolo[3,4-b]quinolin-4-amine, m.p. 160°-163° C.

Workup

  1. stirringThe reaction mixture was stirred overnight
  2. customwas partitioned between CH2Cl2 and water
  3. customThe organic layer was then separated
  4. customdried
  5. customevaporated to dryness
  6. customThe residue was purified by column chromatography on silica gel eluting with ethyl acetate
  7. customfollowed by crystallization from hexane/ether

Sources & evidence

ORD record
ord-578cf4522a0b475fa051651aca3fb270
Source dataset
uspto-grants-1996_01
Patent number
US05488055

Reaction notes

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