Hydrochloric Acid → HCID 58085708, compound

HRID 249721Notes

Reaction equation

HRID 249721 reaction equation
CON(C)[C:4](=[O:24])[C:5]1[CH:10]=[C:9]([S:11]([F:16])([F:15])([F:14])([F:13])[F:12])[CH:8]=[C:7]([NH:17][C:18](=[O:23])[C:19]([F:22])([F:21])[F:20])[CH:6]=1.[CH3:26][Si](C)(C)N[Si](C)(C)C.[Li].C[Mg]Br.Cl>C1COCC1.C(OCC)(=O)C.O>[C:4]([C:5]1[CH:6]=[C:7]([NH:17][C:18](=[O:23])[C:19]([F:20])([F:22])[F:21])[CH:8]=[C:9]([S:11]([F:15])([F:13])([F:14])([F:12])[F:16])[CH:10]=1)(=[O:24])[CH3:26]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 57426343Lithium bis(trimethylsilyl)amideHCID 58085698N-Methoxy-N-methyl-5-pentafluorosulfanyl-3-(2,2,2-trifluoroacetylamino)benzamide2×HCID 178418573HCID 178418573, compound

Product 1

HCID 58085708HCID 58085708, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

N-Methoxy-N-methyl-5-pentafluorosulfanyl-3-(2,2,2-trifluoroacetylamino)benzamide (20 mg) was dissolved in absolute THF (2 ml) and stirred at RT with lithium hexamethyldisilazane solution (45 μl, 1 M in THF) for 30 min. Methylmagnesium bromide solution (17 μl, 3 M in diethyl ether) was then added dropwise with stirring at 0° C. After stirring at RT for 1 h, 1N hydrochloric acid was added dropwise with cooling, followed by water and ethyl acetate. The organic phase was separated off and the water phase was additionally extracted twice with ethyl acetate. The combined ethyl acetate phases were dried over magnesium sulfate, filtered and concentrated. 17 mg of crude product were obtained. After further N-methoxy-N-methyl-5-pentafluorosulfanyl-3-(2,2,2-trifluoroacetylamino)benzamide (60 mg) was reacted in the manner described (crude product obtained: 60 mg), the crude products were combined and purified by means of preparative chromatography. The product-containing fractions were combined, freed from the acetonitrile, rendered basic with saturated sodium hydrogencarbonate solution and extracted three times with ethyl acetate. The combined extracts were dried over magnesium sulfate, filtered and concentrated. 37 mg of the desired compound were obtained.

Workup

  1. stirringAfter stirring at RT for 1 h
  2. temperaturewith cooling
  3. customThe organic phase was separated off
  4. extractionthe water phase was additionally extracted twice with ethyl acetate
  5. dry with materialThe combined ethyl acetate phases were dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custom17 mg of crude product were obtained
  9. custom(crude product obtained: 60 mg)
  10. custompurified by means of preparative chromatography
  11. extractionextracted three times with ethyl acetate
  12. dry with materialThe combined extracts were dried over magnesium sulfate
  13. filtrationfiltered
  14. concentrationconcentrated

Sources & evidence

ORD record
ord-d1f72a19cf3a4334857b203074923e98
Source dataset
uspto-grants-2011_01
Patent number
US07863269B2

Reaction notes

Loading…