Ethyl 3-(2,4-difluorophenyl)-1-(4-methoxybenzyl)-1H-thieno[2,3-c]pyrazole-5-carboxylate → HCID 178468478, compound

HRID 1047616Notes

Reaction equation

HRID 1047616 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:10]2[CH:25]=[C:24]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[S:23][C:11]=2[N:12](CC2C=CC(OC)=CC=2)[N:13]=1>ClCCCl.FC(F)(F)C(O)=O>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:10]2[CH:25]=[C:24]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[S:23][C:11]=2[NH:12][N:13]=1

Participants

4

Reactant 1

HCID 66661061Ethyl 3-(2,4-difluorophenyl)-1-(4-methoxybenzyl)-1H-thieno[2,3-c]pyrazole-5-carboxylate

Product 1

HCID 178468478HCID 178468478, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
100 °C

Procedure

Ethyl 3-(2,4-difluorophenyl)-1-(4-methoxybenzyl)-1H-thieno[2,3-c]pyrazole-5-carboxylate (1.0103 g, 2.358 mmol) was dissolved in a mixture of 1,2-dichloroethane (11.79 ml) and trifluoroacetic acid (11.79 ml) at 25° C. in a sealed heavy-walled reaction vessel. The reaction mixture was heated to 100° C. and allowed to stir for 2 h. The reaction was stopped, cooled to room temperature, and concentrated under reduced pressure. The residue was taken up in ethyl acetate (20 mL), washed with saturated aqueous sodium bicarbonate (1×15 mL) and saturated aqueous sodium chloride (1×15 mL), dried (sodium sulfate), and concentrated under reduced pressure. The crude product was purified by flash chromatography (RediSep SiO2, 120 g column) on a CombiFlash purification system eluting with ethyl acetate-hexanes (0-60%). The title compound (719.0 mg, 2.332 mmol, 99% yield) was recovered as a white solid. LC-MS [M+1]=309.3.

Workup

  1. temperaturecooled to room temperature
  2. concentrationconcentrated under reduced pressure
  3. washwashed with saturated aqueous sodium bicarbonate (1×15 mL) and saturated aqueous sodium chloride (1×15 mL)
  4. dry with materialdried (sodium sulfate)
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified by flash chromatography (RediSep SiO2, 120 g column) on a CombiFlash purification system
  7. washeluting with ethyl acetate-hexanes (0-60%)

Sources & evidence

ORD record
ord-c7f625f37f3c4b4eb504029e20f4ef5b
Source dataset
uspto-grants-2013_10
Patent number
US08569512B2

Reaction notes

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