Sodium Hydroxide → HCID 86661385, compound

HRID 1630659Notes

Reaction equation

HRID 1630659 reaction equation
[F:1][C:2]([F:37])([F:36])[C:3]1[CH:4]=[C:5]([CH:29]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:31]=1)[CH2:6][S:7]([N:10]([CH2:12][C:13]1[CH:17]=[C:16]([C:18]([O:20]C)=[O:19])[N:15]([C:22]2[C:27]([Cl:28])=[CH:26][CH:25]=[CH:24][N:23]=2)[N:14]=1)[CH3:11])(=[O:9])=[O:8].[OH-].[Na+]>CO>[F:36][C:2]([F:1])([F:37])[C:3]1[CH:4]=[C:5]([CH:29]=[C:30]([C:32]([F:35])([F:33])[F:34])[CH:31]=1)[CH2:6][S:7]([N:10]([CH2:12][C:13]1[CH:17]=[C:16]([C:18]([OH:20])=[O:19])[N:15]([C:22]2[C:27]([Cl:28])=[CH:26][CH:25]=[CH:24][N:23]=2)[N:14]=1)[CH3:11])(=[O:9])=[O:8]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86661383HCID 86661383, compound

Product 1

HCID 86661385HCID 86661385, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3.30 g (5.78 mmol) of methyl 3-{[{[3,5-bis(trifluoromethyl)benzyl]sulphonyl}(methyl)amino]methyl}-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxylate were dissolved in 50 ml of methanol, and aqueous sodium hydroxide solution (0.28 g of sodium hydroxide dissolved in 25 ml of water; 6.94 mmol) was added dropwise at 0° C. The reaction mixture was stirred at room temperature for 12 hours. The methanol was then removed under reduced pressure and the aqueous residue was extracted three times with methylene chloride. The organic phase was discarded. The aqueous phase was then adjusted to a pH of 3 using 5% strength hydrochloric acid and extracted with dichloromethane (2×100 ml). The combined organic phases were dried over sodium sulphate. (logP: 3.07; MH+: 557; 1H-NMR (400 MHz, DMSO, δ, ppm): 2.78 (s, 3H), 4.40 (s, 2H), 4.78 (s, 2H), 6.97 (s, 1H), 7.62 (dd, 1H), 8.05 (, 1H), 8.09 (s, 2H), 8.15 (d, 1H), 8.51 (d, 1H).

Workup

  1. customThe methanol was then removed under reduced pressure
  2. extractionthe aqueous residue was extracted three times with methylene chloride
  3. extractionextracted with dichloromethane (2×100 ml)
  4. dry with materialThe combined organic phases were dried over sodium sulphate

Sources & evidence

ORD record
ord-c2bb640189d643109bff73220dbc547b
Source dataset
uspto-grants-2014_07
Patent number
US08791139B2

Reaction notes

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