Dimethylformamide → 1-[3-(3-dimethylamino-2-methylpropoxy)phenyl]-3-phenyl-1H-pyrazolo[3,4-b]pyridine.maleate

HRID 1084834Notes

Reaction equation

HRID 1084834 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([N:8]2[C:12]3=[N:13][CH:14]=[CH:15][CH:16]=[C:11]3[C:10]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[N:9]2)[CH:5]=[CH:6][CH:7]=1.[CH3:23][N:24]([CH3:30])[CH2:25][CH:26]([CH3:29])[CH2:27]Cl.[C:31](=[O:34])([O-:33])[O-].[K+].[K+].CN(C)C=[O:40]>>[CH3:23][N:24]([CH3:30])[CH2:25][CH:26]([CH3:29])[CH2:27][O:1][C:2]1[CH:3]=[C:4]([N:8]2[C:12]3=[N:13][CH:14]=[CH:15][CH:16]=[C:11]3[C:10]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)=[N:9]2)[CH:5]=[CH:6][CH:7]=1.[C:2]([O-:1])(=[O:40])/[CH:7]=[CH:6]\[C:31]([O-:33])=[O:34]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 909063-Chloro-2-methylpropyl(dimethyl)amineHCID 147962521-(3-hydroxyphenyl)-3-phenyl-1H-pyrazolo[3,4-b]pyridine

Product 1

HCID 867447151-[3-(3-dimethylamino-2-methylpropoxy)phenyl]-3-phenyl-1H-pyrazolo[3,4-b]pyridine.maleate

Conditions

Temperature
100 °C

Procedure

In 70 ml of dimethylformamide were suspended 4.0 g of 1-(3-hydroxyphenyl)-3-phenyl-1H-pyrazolo[3,4-b]pyridine, 2.6 g of 3-dimethylamino-2-methylpropylchloride and 2.3 g of potassium carbonate. The mixture was stirred at 100° C. for 6 hours. The solvent was distilled off under reduced pressure. By adding maleic acid, the residue was converted into the salt. The obtained crude crystals were recrystallized from a mixed solvent of ethyl acetate and ethanol to give 5.2 g of 1-[3-(3-dimethylamino-2-methylpropoxy)phenyl]-3-phenyl-1H-pyrazolo[3,4-b]pyridine·maleate, m.p. 134°-136° C.

Workup

  1. distillationThe solvent was distilled off under reduced pressure
  2. additionBy adding maleic acid
  3. customThe obtained crude crystals
  4. customwere recrystallized from a mixed solvent of ethyl acetate and ethanol

Sources & evidence

ORD record
ord-237e117d73634362be1ff1f2c2c80e6d
Source dataset
uspto-grants-1991_04
Patent number
US05006520

Reaction notes

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