Methanol → HCID 59632370, compound

HRID 2369105Notes

Reaction equation

HRID 2369105 reaction equation
C([O:3][C:4]([C:6]1[CH:10]=[C:9]([C:11]2[S:12][C:13]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([S:22]([CH3:25])(=[O:24])=[O:23])[CH:17]=3)=[CH:14][CH:15]=2)[N:8]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[C:32]([F:35])([F:34])[F:33])[N:7]=1)=[O:5])C.[OH-].[Na+].CO>CCOC(C)=O>[CH3:25][S:22]([C:18]1[CH:17]=[C:16]([C:13]2[S:12][C:11]([C:9]3[N:8]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=4[C:32]([F:33])([F:34])[F:35])[N:7]=[C:6]([C:4]([OH:5])=[O:3])[CH:10]=3)=[CH:15][CH:14]=2)[CH:21]=[CH:20][CH:19]=1)(=[O:24])=[O:23]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 68656642HCID 68656642, compound

Product 1

HCID 59632370HCID 59632370, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a 100 mL round bottom flask attached with condenser was added 5-[5-(3-Methanesulfonyl-phenyl)-thiophen-2-yl]-1-(2-trifluoromethyl-phenyl)-1H-pyrazole-3-carboxylic acid ethyl ester (2.52 g, 4.98 mmol), 1N aq NaOH (30 mL), and MeOH (25 mL). The reaction solution was stared at 55° C. for 1.5 hr prior to TLC analysis. The reaction solution was diluted with EtOAc (200 mL), poured into a separately funnel and the organic phase was partitioned. The aqueous phase was neutralized by the addition of aq 1 N HCl and extracted with EtOAc (70 mL×2). The combined organic phase was dried over Na2SO4, filtered into a round bottom flask and concentrated on the Rotavapor. The crude residue was chromatographed thru a 25 g SiO2 column using a mobile phase gradient of 100% Hx to 85% EtOAc to afford 1.35 g (55% yield) title compound. MS (ES) 493.1 [M+H]+.

Workup

  1. customTo a 100 mL round bottom flask attached with condenser
  2. additionpoured into a separately funnel
  3. customthe organic phase was partitioned
  4. additionThe aqueous phase was neutralized by the addition of aq 1 N HCl
  5. extractionextracted with EtOAc (70 mL×2)
  6. dry with materialThe combined organic phase was dried over Na2SO4
  7. filtrationfiltered into a round bottom flask
  8. concentrationconcentrated on the Rotavapor
  9. customThe crude residue was chromatographed

Sources & evidence

ORD record
ord-a42810a19551440ca149e17c1647a693
Source dataset
uspto-grants-2014_04
Patent number
US08703805B2

Reaction notes

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