Dimethylformamide → HCID 86744713, compound

HRID 1084832Notes

Reaction equation

HRID 1084832 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([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:4][CH:3]=1.[CH3:23][N:24]([CH3:29])[CH2:25][CH2:26][CH2:27]Cl.[C:30](=[O:33])([O-:32])[O-].[K+].[K+].CN(C)C=[O:39]>>[CH3:23][N:24]([CH3:29])[CH2:25][CH2:26][CH2:27][O:1][C:2]1[CH:3]=[CH:4][C:5]([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:6][CH:7]=1.[C:2]([O-:1])(=[O:39])/[CH:3]=[CH:4]\[C:30]([O-:32])=[O:33]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 669603-Chloro-N,N-dimethyl-1-propanamineHCID 14796259HCID 14796259, compound

Product 1

HCID 86744713HCID 86744713, compound

Conditions

Temperature
100 °C

Procedure

In 100 ml of dimethylformamide were suspended 7.0 g of 1-(4-hydroxyphenyl)-3-phenyl-1H-pyrazolo[3,4-b]pyridine, 3.6 g of 3-dimethylaminopropylchloride and 3.7 g of potassium carbonate. The mixture was stirred at 100° C. for 4 hours. After the solvent was distilled off under reduced pressure, the residue was extracted with chloroform-water. The organic layer was concentrated, and the residue was purified by silica gel column chromatography (eluent: chloroform : methanol=20:1). Thereafter, by adding maleic acid, the purified product was converted into the salt. The obtained crude crystals were recrystallized from ethyl acetate to give 7.2 g of 1-[4-(3-dimethylaminopropoxy)phenyl]-3-phenyl-1H-pyrazolo[3,4-b]pyridine·maleate, m.p. 133°-136° C.

Workup

  1. distillationAfter the solvent was distilled off under reduced pressure
  2. extractionthe residue was extracted with chloroform-water
  3. concentrationThe organic layer was concentrated
  4. customthe residue was purified by silica gel column chromatography (eluent: chloroform : methanol=20:1)
  5. additionThereafter, by adding maleic acid
  6. customThe obtained crude crystals
  7. customwere recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-a8d85c776d384bfdb53be66d42c9d2ee
Source dataset
uspto-grants-1991_04
Patent number
US05006520

Reaction notes

Loading…