Epichlorohydrin → HCID 86749231, compound

HRID 1586151Notes

Reaction equation

HRID 1586151 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) is stirred for 30 minutes and then epichlorohydrin (1.5 ml) is added. The reaction mixture is stirred overnight and then is partitioned between CH2Cl2 and water. The organic layer is then separated, dried and evaporated to dryness. The residue is 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 is stirred overnight
  2. customis partitioned between CH2Cl2 and water
  3. customThe organic layer is then separated
  4. customdried
  5. customevaporated to dryness
  6. customThe residue is purified by column chromatography on silica gel eluting with ethyl acetate
  7. customfollowed by crystallization from hexane/ether

Sources & evidence

ORD record
ord-2002e0dc0e8b45efaf67369481552e7a
Source dataset
uspto-grants-1999_08
Patent number
US05942520

Reaction notes

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