Epichlorohydrin → HCID 86749231, compound

HRID 375873Notes

Reaction equation

HRID 375873 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 (2 g), DMSO (30 ml) and KOH (2 g) was stirred at room temperature for 0.5 hours, then epichlorohydrin (0.49 ml) was added and the mixture was stirred overnight. The reaction mixture was partitioned between CH2Cl2 and water, and then the CH2Cl2 layer was separated and evaporated. The residue was purified by column chromatography on silica gel eluting with ethyl acetate to afford the product which was combined with the product from a similar experimental. The combined material was purified further by column chromatography on silica gel eluting with 90% ether/t-butylmethylether, followed by crystallization from ether, to afford 1-ethyl-6-(2,3-epoxypropoxy)-N-(cyclohexylmethyl)-1H-pyrazolo[3,4-b]quinolin-4amine, m.p. 168°-170° C.

Workup

  1. stirringthe mixture was stirred overnight
  2. customThe reaction mixture was partitioned between CH2Cl2 and water
  3. customthe CH2Cl2 layer was separated
  4. customevaporated
  5. customThe residue was purified by column chromatography on silica gel eluting with ethyl acetate
  6. customto afford the product which
  7. customThe combined material was purified further by column chromatography on silica gel eluting with 90% ether/t-butylmethylether
  8. customfollowed by crystallization from ether

Sources & evidence

ORD record
ord-4a0e5a502b9648d7a5548d170e8ab278
Source dataset
uspto-grants-1996_01
Patent number
US05488055

Reaction notes

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