Acetic Anhydride → HCID 67393385, compound

HRID 1927967Notes

Reaction equation

HRID 1927967 reaction equation
[C:1]([NH:5][S:6]([C:9]1[CH:10]=[C:11]([C:15]2[N:20]=[C:19]([C:21]([NH:23]O)=[NH:22])[CH:18]=[CH:17][CH:16]=2)[CH:12]=[CH:13][CH:14]=1)(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:25]([O:28]C(=O)C)(=[O:27])[CH3:26].[H][H]>C(O)(=O)C.[Pd]>[C:25]([O-:28])(=[O:27])[CH3:26].[C:1]([NH:5][S:6]([C:9]1[CH:10]=[C:11]([C:15]2[N:20]=[C:19]([C:21]([NH2:23])=[NH2+:22])[CH:18]=[CH:17][CH:16]=2)[CH:12]=[CH:13][CH:14]=1)(=[O:8])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 178418361HCID 178418361, compoundHCID 178449977HCID 178449977, compound

Product 1

HCID 67393385HCID 67393385, compoundYield 148%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
23 °C

Procedure

To a mixture of 6-(3-tert-butylsulfamoyl-phenyl)-N-hydroxy-pyridine-2-carboxamidine (Example C.7) (830 mg, 2.38 mmol) in acetic acid (10 ml) at 23° C. was added acetic anhydride (0.34 ml, 3.57 mmol) and the mixture was stirred at 23° C. for 10 min, then 10% Pd on charcoal (84 mg, 0.79 mmol) was added and the mixture was hydrogenated (1 bar hydrogen) at 23° C. for 24 h. The catalyst was filtered off, washed with acetic acid and the solvents were evaporated to give the title compound (1.38 g, 148%, contains excess acetic acid) as a light yellow oil, which was used without further purification (cf. Synth. Commun. 1996, 26(23), 4351). MS (ISP) 333.1 [(M+H)+].

Workup

  1. customat 23° C.
  2. customat 23° C.
  3. customfor 24 h
  4. filtrationThe catalyst was filtered off
  5. washwashed with acetic acid
  6. customthe solvents were evaporated

Sources & evidence

ORD record
ord-36f356cff47f45a28322cd6b0e8eff3e
Source dataset
uspto-grants-2012_05
Patent number
US08183262B2

Reaction notes

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