Triethylamine → HCID 58137447, compound

HRID 1258507Notes

Reaction equation

HRID 1258507 reaction equation
FC(F)(F)C(O)=O.[NH2:8][C:9]1[CH:10]=[C:11]([C:21](=[O:23])[CH3:22])[CH:12]=[C:13]([S:15]([F:20])([F:19])([F:18])([F:17])[F:16])[CH:14]=1.C(N(CC)CC)C.[CH3:31][S:32](Cl)(=[O:34])=[O:33].C(=O)([O-])O.[Na+]>C(Cl)Cl.O.C(OCC)(=O)C>[CH3:31][S:32]([N:8]([S:32]([CH3:31])(=[O:34])=[O:33])[C:9]1[CH:10]=[C:11]([C:21](=[O:23])[CH3:22])[CH:12]=[C:13]([S:15]([F:20])([F:16])([F:17])([F:18])[F:19])[CH:14]=1)(=[O:34])=[O:33]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chloride2×HCID 516892Sodium BicarbonateHCID 86650835HCID 86650835, compound

Product 1

HCID 58137447HCID 58137447, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-[3-Amino-5-(pentafluorosulfanyl)phenyl]ethanone trifluoroacetic acid salt (100 mg, example 4d) was dissolved in methylene chloride (10 ml), triethylamine (120 μl) was added, and methanesulfonyl chloride (21 μl) was added while stirring. After 2 h, the mixture was left to stand overnight and then further methanesulfonyl chloride (20 μl) was added. After a further 2 h, the solvent was drawn off and the residue was taken up with ethyl acetate and water, and adjusted to pH 9 with saturated sodium hydrogencarbonate solution, and the aqueous phase was extracted twice more with ethyl acetate. The combined extracts were dried over magnesium sulfate, filtered and concentrated. The residue was purified by means of preparative HPLC. The product-containing fractions were combined, freed of the acetonitrile and freeze-dried. 36 mg of the title compound were obtained.

Workup

  1. waitthe mixture was left
  2. waitto stand overnight
  3. waitAfter a further 2 h
  4. extractionthe aqueous phase was extracted twice more with ethyl acetate
  5. dry with materialThe combined extracts were dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by means of preparative HPLC
  9. customfreeze-dried

Sources & evidence

ORD record
ord-e919a7fd315e4119b2df77dee2c99250
Source dataset
uspto-grants-2013_06
Patent number
US08466169B2

Reaction notes

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