Dimethylformamide → HCID 86744719, compound

HRID 1084843Notes

Reaction equation

HRID 1084843 reaction equation
[CH3:1][N:2]([CH3:22])[CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[C:21]3[C:16](=[N:17][CH:18]=[CH:19][CH:20]=3)[NH:15][N:14]=2)=[CH:9][CH:8]=1.[C:23](=[O:26])([O-:25])[O-].[K+].[K+].[Cl:29][C:30]1[CH:37]=[CH:36][C:33]([CH2:34]Cl)=[CH:32][CH:31]=1.CN(C)C=[O:41]>C1(C)C=CC=CC=1>[Cl:29][C:30]1[CH:37]=[CH:36][C:33]([CH2:34][N:15]2[C:16]3=[N:17][CH:18]=[CH:19][CH:20]=[C:21]3[C:13]([C:10]3[CH:11]=[CH:12][C:7]([O:6][CH2:5][CH2:4][CH2:3][N:2]([CH3:1])[CH3:22])=[CH:8][CH:9]=3)=[N:14]2)=[CH:32][CH:31]=1.[C:7]([O-:41])(=[O:6])/[CH:8]=[CH:9]\[C:23]([O-:25])=[O:26]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 77231-Chloro-4-(chloromethyl)benzeneHCID 11430Potassium CarbonateHCID 178483568HCID 178483568, compound

Product 1

HCID 86744719HCID 86744719, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
50 °C

Procedure

In 20 ml of dimethylformamide were suspended 6.0 g of 3-[4-(3-dimethylaminopropoxy)phenyl]-1H-pyrazolo[3,4-b]pyridine and 4.1 g of potassium carbonate. While the mixture was stirred under heating at 50° C., 3.9 g of 4-chlorobenzylchloride dissolved in 5 ml of toluene was added. After the mixture was stirred at 50° C. for 1 hour, the mixture was extracted with toluene-water. The organic layer was concentrated. By adding maleic acid to the residue, the salt was obtained. The obtained crude crystals were recrystallized from ethanol to give 4.5 g of 1-(4-chlorobenzyl)-3-[4-(3-dimethylaminopropoxy)phenyl]-1H-pyrazolo[3,4-b]pyridine·maleate, m.p. 136°-138° C.

Workup

  1. additionwas added
  2. stirringAfter the mixture was stirred at 50° C. for 1 hour
  3. extractionthe mixture was extracted with toluene-water
  4. concentrationThe organic layer was concentrated
  5. additionBy adding maleic acid to the residue
  6. customthe salt was obtained
  7. customThe obtained crude crystals
  8. customwere recrystallized from ethanol

Sources & evidence

ORD record
ord-caa3e371da694f46b7adfaacfded1cb2
Source dataset
uspto-grants-1991_04
Patent number
US05006520

Reaction notes

Loading…