Acetic Anhydride → HCID 9998367, compound

HRID 915504Notes

Reaction equation

HRID 915504 reaction equation
C(N(C(C)C)CC)(C)C.[C:10](OC(=O)C)(=[O:12])[CH3:11].[CH3:17][NH:18][C:19]([C:21]1[C:25]2[CH:26]=[C:27]([O:31][CH3:32])[C:28]([NH2:30])=[CH:29][C:24]=2[O:23][C:22]=1[C:33]1[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=1)=[O:20]>ClC(Cl)Cl>[CH3:17][NH:18][C:19]([C:21]1[C:25]2[CH:26]=[C:27]([O:31][CH3:32])[C:28]([NH:30][C:10](=[O:12])[CH3:11])=[CH:29][C:24]=2[O:23][C:22]=1[C:33]1[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=1)=[O:20]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 81531DiisopropylethylamineHCID 10448339HCID 10448339, compound

Product 1

HCID 9998367HCID 9998367, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Diisopropylethylamine (83.2 μL, 477 μmol), followed by acetic anhydride (239 μmol) were added to a solution of 6-amino-2-(4-fluoro-phenyl)-5-methoxy-benzofuran-3-carboxylic acid methylamide, prepared according to Example 17 (75 mg, 239 μmol) in dry trichloromethane (3 mL). After one hour, the reaction was quenched with water (3 mL). After concentration to dryness, the crude oil was purified by HPLC (reverse phase, C18, acetonitrile/water with 0.1% acetic acid) to provide 73 mg (87%) of the title compound.

Workup

  1. customprepared
  2. customthe reaction was quenched with water (3 mL)
  3. concentrationAfter concentration to dryness
  4. customthe crude oil was purified by HPLC (reverse phase, C18, acetonitrile/water with 0.1% acetic acid)

Sources & evidence

ORD record
ord-c0e290b876cd4c9ebb74a575665f57cd
Source dataset
uspto-grants-2007_09
Patent number
US07265152B2

Reaction notes

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