Dimethylformamide → HCID 86744717, compound

HRID 1084836Notes

Reaction equation

HRID 1084836 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:10]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([OH:23])[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]>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:10]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH2:28][CH2:27][CH2:26][N:25]([CH3:30])[CH3:24])[CH:18]=3)[N:9]=2)=[CH:6][CH:7]=1.[C:19]([O-:23])(=[O:40])/[CH:20]=[CH:21]\[C:31]([O-:33])=[O:34]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 669603-Chloro-N,N-dimethyl-1-propanamineHCID 14796261HCID 14796261, compound

Product 1

HCID 86744717HCID 86744717, compound

Conditions

Temperature
100 °C

Procedure

In 15 ml of dimethylformamide were suspended 5.3 g of 3-(4-fluorophenyl)-1-(3-hydroxyphenyl)-1H-indazole, 2.5 g of 3-dimethylaminopropylchloride and 2.7 g of potassium carbonate. The mixture was stirred at 100° C. for 4 hours, and then it was extracted with toluene-water. After the organic layer was concentrated, maleic acid was added to the residue to obtain the salt. The obtained crude crystals were recrystallized from ethyl acetate to give 5.0 g of 3-(4-fluorophenyl)-1-[3-(3-dimethylaminopropoxy)phenyl]-1H-indazole·maleate, m.p. 110°-112° C.

Workup

  1. extractionit was extracted with toluene-water
  2. concentrationAfter the organic layer was concentrated
  3. additionmaleic acid was added to the residue
  4. customto obtain the salt
  5. customThe obtained crude crystals
  6. customwere recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-9631de0d9a3b4451b864bb2133c9ad77
Source dataset
uspto-grants-1991_04
Patent number
US05006520

Reaction notes

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