Tetrahydrofuran → HCID 59428113, compound

HRID 218192Notes

Reaction equation

HRID 218192 reaction equation
C([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([C:11]2[C:16]([NH:17][S:18]([C:21]3[CH:26]=[CH:25][C:24]([C:27]([CH3:30])([CH3:29])[CH3:28])=[CH:23][CH:22]=3)(=[O:20])=[O:19])=[CH:15][C:14]([Cl:31])=[CH:13][N:12]=2)[CH:10]=1)=[O:5])C.[OH-].[Na+].C1COCC1>C(O)(=O)C>[C:27]([C:24]1[CH:25]=[CH:26][C:21]([S:18]([NH:17][C:16]2[C:11]([N:9]3[CH:10]=[C:6]([C:4]([OH:5])=[O:3])[CH:7]=[N:8]3)=[N:12][CH:13]=[C:14]([Cl:31])[CH:15]=2)(=[O:19])=[O:20])=[CH:22][CH:23]=1)([CH3:30])([CH3:28])[CH3:29]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 25134467HCID 25134467, compound

Product 1

HCID 59428113HCID 59428113, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
80 °C

Procedure

A 25 mL scintillation vial was charged with 1-[3-(4-tert-butyl-benzenesulfonylamino)-5-chloro-pyridin-2-yl]-1H-pyrazole-4-carboxylic acid ethyl ester (synthesized according to general procedure D, 93 mg, 0.2 mmol), NaOH (2 mL, 1.0 M solution in water), and THF (3 mL). The vial was sealed and stirred at 80° C. for 16 hours. The reaction solution was subsequently neutralized to pH=5 with glacial acetic acid. The mixture was extracted with ethyl acetate (2×10 mL) and the combined organics were concentrated in vacuo. The resultant residue was purified via preparative HPLC to afford 1-[3-(4-tert-butyl-benzenesulfonylamino)-5-chloro-pyridin-2-yl]-1H-pyrazole-4-carboxylic acid as a white powder: MS (ES) M+H expected 435.1, found 435.0.

Workup

  1. customThe vial was sealed
  2. extractionThe mixture was extracted with ethyl acetate (2×10 mL)
  3. concentrationthe combined organics were concentrated in vacuo
  4. customThe resultant residue was purified via preparative HPLC

Sources & evidence

ORD record
ord-4ad4d452798a48d5b0dd09221ba9c042
Source dataset
uspto-grants-2012_06
Patent number
US08198309B2

Reaction notes

Loading…