Dimethylformamide → HCID 15117091, compound

HRID 359022Notes

Reaction equation

HRID 359022 reaction equation
Cl.[N:2]1([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][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=3)[N:9]=2)[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.Br[CH:28]([OH:30])[CH3:29].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[OH:30][CH2:28][CH2:29][N:5]1[CH2:6][CH2:7][N:2]([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][C:20]([C:23]([F:26])([F:24])[F:25])=[CH:19][CH:18]=3)[N:9]=2)[CH2:3][CH2:4]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 14202443Ethanol, 1-bromo-HCID 19887050HCID 19887050, compound

Product 1

HCID 15117091HCID 15117091, compoundYield 44.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A stirred mixture of 5.5 g of 3-(1-piperazinyl)-1-[4(trifluoromethyl)phenyl]-1H-indazole hydrochloride, 2.3 g of bromoethanol, 2.5 g of potassium carbonate and 60 ml of dimethylformamide was heated, under nitrogen, at 70°-75° for 16 hours. The reaction mixture was poured into water and the aqueous mixture extracted with ethyl acetate. The extract was washed with water, dried over anhydrous magnesium sulfate and concentrated to an oil. The oil was chromatographed on silica gel utilizing a Water's Model 500 High Pressure Liquid Chromatograph and eluting with dichloromethane/methanol (6%). Evaporation of the appropriate fractions gave an oil which solidified upon standing. Recrystallization of the solid from hexane (2×) gave 2.5 g (40%) of 3-[4-(2-hydroxyethyl)-1piperazinyl-]-1-[4-(trifluoromethyl)phenyl]-1H-indazole, mp 82°-84°.

Workup

  1. temperaturewas heated, under nitrogen, at 70°-75° for 16 hours
  2. extractionthe aqueous mixture extracted with ethyl acetate
  3. washThe extract was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated to an oil
  6. customThe oil was chromatographed on silica gel utilizing a Water'
  7. washeluting with dichloromethane/methanol (6%)
  8. customEvaporation of the appropriate fractions
  9. customgave an oil which
  10. customRecrystallization of the solid from hexane (2×)

Sources & evidence

ORD record
ord-6b501b61b4c64d64887a9d0bf6e1131b
Source dataset
uspto-grants-1991_03
Patent number
US04999356

Reaction notes

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