Hydrochloric Acid → HCID 136395590, compound

HRID 746792Notes

Reaction equation

HRID 746792 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:16]2[CH:21]=[CH:20][C:19]([C:22]3[CH:27]=[CH:26][N:25]=[CH:24][C:23]=3[NH:28][S:29]([CH:32]([CH3:34])[CH3:33])(=[O:31])=[O:30])=[CH:18][CH:17]=2)[CH:5]=[C:6]([F:15])[C:7]=1[O:8]C(=O)C(C)(C)C.[OH-].[Na+].Cl>C1COCC1.C(O)C>[F:1][C:2]1[CH:3]=[C:4]([C:16]2[CH:21]=[CH:20][C:19]([C:22]3[CH:27]=[CH:26][N:25]=[CH:24][C:23]=3[NH:28][S:29]([CH:32]([CH3:34])[CH3:33])(=[O:30])=[O:31])=[CH:18][CH:17]=2)[CH:5]=[C:6]([F:15])[C:7]=1[OH:8]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 69253850HCID 69253850, compound

Product 1

HCID 136395590HCID 136395590, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Dissolve 2,2-Dimethyl-propionic acid 3,5-difluoro-4′-[3-(propane-2-sulfonylamino)-pyridin-4-yl]-biphenyl-4-yl ester in THF (9 ml) and ethanol (1 ml). Add NaOH 2N (10 ml) and heat the mixture to 60° C. for 7 h. Evaporate solvents and add HCl 3N to acidify the mixture. Apply the acidic mixture to 2 g SCX cartridge. Elute the SCX cartridge with methanol (×3) to remove non-basic impurities. Elute the product with 2N ammonia in methanol to afford, after evaporation, 55.2 mg of the title compound as a yellow solid (50% yield). MS (ES−): 403.

Workup

  1. washElute the SCX cartridge with methanol (×3)
  2. customto remove non-basic impurities
  3. washElute the product with 2N ammonia in methanol
  4. customto afford

Sources & evidence

ORD record
ord-0d1581fb1e26482b861b8df59179396f
Source dataset
uspto-grants-2008_07
Patent number
US07393868B2

Reaction notes

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