Water → HCID 86661383, compound

HRID 1630658Notes

Reaction equation

HRID 1630658 reaction equation
[Cl:1][C:2]1[C:3]([N:8]2[C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][C:10]([CH2:17]S(C)(=O)=O)=[N:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1.[F:22][C:23]([F:41])([F:40])[C:24]1[CH:25]=[C:26]([CH2:34][S:35]([NH:38][CH3:39])(=[O:37])=[O:36])[CH:27]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:29]=1.C(=O)([O-])[O-].[K+].[K+].O>C(#N)C>[F:41][C:23]([F:22])([F:40])[C:24]1[CH:25]=[C:26]([CH:27]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:29]=1)[CH2:34][S:35]([N:38]([CH2:17][C:10]1[CH:11]=[C:12]([C:13]([O:15][CH3:16])=[O:14])[N:8]([C:3]2[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][N:4]=2)[N:9]=1)[CH3:39])(=[O:36])=[O:37]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 66659743HCID 66659743, compoundHCID 86661384HCID 86661384, compound

Product 1

HCID 86661383HCID 86661383, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

5.00 g (14.4 mmol) of methyl 1-(3-chloropyridin-2-yl)-3-[(methylsulphonyl)methyl]-1H-pyrazole-5-carboxylate were dissolved in 50 ml of acetonitrile, and 4.64 g (14.4 mmol) of 1-[3,5-bis(trifluoromethyl)phenyl]-N-methylmethanesulphonamide were added a little at a time at room temperature. Then 2.40 g (17.35 mmol) of potassium carbonate were added to the reaction solution, and the mixture was stirred at 50° C. for 12 hours. After cooling to room temperature, the reaction solution was freed from the solvent under reduced pressure. 250 ml of water were added to the residue, and the mixture was extracted with ethyl acetate (3×100 ml). The combined organic phases were dried over sodium sulphate. The solvent was removed under reduced pressure and the residue was purified by chromatography. (logP: 3.83; MH+: 571; 1H-NMR (400 MHz, DMSO, δ, ppm): 2.79 (s, 3H), 3.74 (s, 3H), 4.43 (s, 2H), 4.80 (s, 2H), 7.06 (s, 1H), 7.70 (dd, 1H), 8.12 (s, 2H), 8.15 (s, 1H), 8.26 (d, 1H), 8.57 (d, 1H).

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionthe mixture was extracted with ethyl acetate (3×100 ml)
  3. dry with materialThe combined organic phases were dried over sodium sulphate
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was purified by chromatography

Sources & evidence

ORD record
ord-0ca4fc35f85042638ee3326d6f200b0a
Source dataset
uspto-grants-2014_07
Patent number
US08791139B2

Reaction notes

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