Acetic Anhydride → HCID 69743165, compound

HRID 2181717Notes

Reaction equation

HRID 2181717 reaction equation
[C:1]([C:3]1[C:4]([C:24]([F:27])([F:26])[F:25])=[N:5][N:6]([C:14]2[N:19]=[CH:18][C:17]([S:20]([NH2:23])(=[O:22])=[O:21])=[CH:16][CH:15]=2)[C:7]=1[NH:8][CH2:9][C:10]([CH3:13])([CH3:12])[CH3:11])#[N:2].[C:28](OC(=O)C)(=[O:30])[CH3:29].C(N(CC)CC)C.[Na:42].[OH-].[Na+]>C(Cl)Cl.C(O)C>[Na:42].[C:28]([NH:23][S:20]([C:17]1[CH:18]=[N:19][C:14]([N:6]2[C:7]([NH:8][CH2:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[C:3]([C:1]#[N:2])[C:4]([C:24]([F:26])([F:27])[F:25])=[N:5]2)=[CH:15][CH:16]=1)(=[O:21])=[O:22])(=[O:30])[CH3:29]

Participants

8

Reactant 5

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 5360545SodiumHCID 44406358HCID 44406358, compound

Product 1

HCID 69743165HCID 69743165, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

6-[4-Cyano-5-(2,2-dimethyl-propylamino)-3-trifluoromethyl-pyrazol-1-yl]-pyridine-3-sulfonic acid amide (166.3 mg, 0.413 mMol), was dissolved in methylene chloride (10 ml) and stirred under nitrogen. Acetic anhydride (126.5 mg, 1.239 mMol), triethylamine (49.3 mg, 0.49 mMol) and N,N-dimethylaminopyridine (25.2 mg, 0.5 mMol) were added into the methylene chloride solution, and stirred for 18 hours. The reaction mixture was washed with water and brine, dried with magnesium sulfate, filtered, and evaporated. The residue was chromatographed on silica, eluting with 0.75% methanol/methylene chloride, to give a free acid in 80% yield. The free acid was converted to the sodium salt by reacting the free acid with one equivalent of sodium hydroxide in ethanol, evaporation, and drying under high vacuum. The desired product was isolated by chromatography on silica gel column. MS: 443.5 ES, r.t.: 3.0 minutes.

Workup

  1. stirringstirred for 18 hours
  2. washThe reaction mixture was washed with water and brine
  3. dry with materialdried with magnesium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was chromatographed on silica
  7. washeluting with 0.75% methanol/methylene chloride
  8. customto give a free acid in 80% yield
  9. customdrying under high vacuum

Sources & evidence

ORD record
ord-532e4c04f464449296abb07dc67f4981
Source dataset
uspto-grants-2005_05
Patent number
US06894067B2

Reaction notes

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