Dimethylformamide → HCID 86744714, compound

HRID 1084833Notes

Reaction equation

[Br: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]([OH:23])=[CH:19][CH:18]=3)[N:9]=2)=[CH:4][CH:3]=1.[CH2:24]([N:26]([CH2:30][CH3:31])[CH2:27][CH2:28]Cl)[CH3:25].[C:32](=[O:35])([O-:34])[O-].[K+].[K+].CN(C)C=[O:41]>>[Br: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]([O:23][CH2:25][CH2:24][N:26]([CH2:30][CH3:31])[CH2:27][CH3:28])=[CH:19][CH:18]=3)[N:9]=2)=[CH:4][CH:3]=1.[C:20]([O-:23])(=[O:41])/[CH:21]=[CH:22]\[C:32]([O-:34])=[O:35]

Participants

Reactant 4

HCID 6228Dimethylformamide

HCID 11430Potassium Carbonate

HCID 13364Diethylaminoethyl chloride

HCID 15158064HCID 15158064, compound

Product 1

HCID 86744714HCID 86744714, compound

Conditions

Temperature: 100 °C

Procedure

In 60 ml of dimethylformamide were suspended 4.0 g of 3-(4-bromophenyl)-1-(4-hydroxyphenyl)-1H-pyrazolo[3,4-b]pyridine, 1.8 g of 2-diethylaminoethylchloride and 1.7 g of potassium carbonate. The mixture was stirred at 100° C. for 6 hours. After the solvent was distilled off under reduced pressure, the residue was extracted with toluene-water. The organic layer was concentrated. By adding maleic acid, the residue was corverted into the salt. The obtained crude crystals were recrystallized from ethyl acetate to give 3.0 g of 3-(4-bromophenyl)-1-[4-(2-diethylaminoethoxy)phenyl]-1H-pyrazolo[3,4-b]pyridine·maleate, m.p. 135°-140° C.

Workup

distillationAfter the solvent was distilled off under reduced pressure
extractionthe residue was extracted with toluene-water
concentrationThe organic layer was concentrated
additionBy adding maleic acid
customThe obtained crude crystals
customwere recrystallized from ethyl acetate

Sources & evidence

ORD record: ord-451219abdd6344cfa4ed884f82eb0727
Source dataset: uspto-grants-1991_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05006520

Reaction notes

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