Dimethylformamide → HCID 86744716, compound

HRID 1084835Notes

Reaction equation

HRID 1084835 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:11](=[N:12][CH:13]=[CH:14][CH:15]=3)[N:10]([C:17]3[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=3)[N:9]=2)=[CH:4][CH:3]=1.[CH3:24][N:25]([CH3:30])[CH2:26][CH2:27][CH2:28]Cl.[C:31](=[O:34])([O-:33])[O-].[K+].[K+].CN(C)C=[O:40]>>[CH3:24][N:25]([CH3:30])[CH2:26][CH2:27][CH2:28][O:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:16]3[C:11](=[N:12][CH:13]=[CH:14][CH:15]=3)[N:10]([C:17]3[CH:18]=[CH:19][C:20]([CH3:23])=[CH:21][CH:22]=3)[N:9]=2)=[CH:6][CH:7]=1.[C:2]([O-:1])(=[O:40])/[CH:3]=[CH:4]\[C:31]([O-:33])=[O:34]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 669603-Chloro-N,N-dimethyl-1-propanamineHCID 135621434HCID 135621434, compound

Product 1

HCID 86744716HCID 86744716, compound

Conditions

Temperature
100 °C

Procedure

In 15 ml of dimethylformamide were suspended 4.5 g of 3-(4-hydroxyphenyl)-1-(4-methylphenyl)-1H-pyrazolo[3,4-b]pyridine, 2.2 g of 3-dimethylaminopropylchloride and 2.3 g of potassium carbonate. After the mixture was stirred at 100° C. for 4 hours, it was extracted with toluene-water. The organic layer was concentrated. By adding maleic acid to the residue, it was converted to the salt. The obtained crude crystals were recrystallized from ethanol to give 4.0 g of 3-[4-(3-dimethylaminopropoxy)phenyl]-1-(4-methylphenyl)-1H-pyrazolo[3,4-b]pyridine·maleate, m.p. 138°-140° C.

Workup

  1. extractionit was extracted with toluene-water
  2. concentrationThe organic layer was concentrated
  3. additionBy adding maleic acid to the residue, it
  4. customThe obtained crude crystals
  5. customwere recrystallized from ethanol

Sources & evidence

ORD record
ord-f449ff16f6b04d6ebd37ef8c4df8f64f
Source dataset
uspto-grants-1991_04
Patent number
US05006520

Reaction notes

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