Acetic Anhydride → HCID 6539894, compound

HRID 1921049Notes

Reaction equation

HRID 1921049 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]([N:12]([CH3:24])[CH2:13][C:14]2[N:15]([CH3:23])[C:16]3[C:21]([CH:22]=2)=[CH:20][CH:19]=[CH:18][CH:17]=3)=[O:11])=[CH:4][CH:3]=1.C([O-])(O)=O.[Na+].[C:30](OC(=O)C)(=[O:32])[CH3:31]>C1COCC1>[C:30]([NH:1][C:2]1[N:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]([N:12]([CH3:24])[CH2:13][C:14]2[N:15]([CH3:23])[C:16]3[C:21]([CH:22]=2)=[CH:20][CH:19]=[CH:18][CH:17]=3)=[O:11])=[CH:4][CH:3]=1)(=[O:32])[CH3:31]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 52877203-(6-Aminopyridin-3-Yl)-N-Methyl-N-((1-Methyl-1h-Indol-2-Yl)Methyl)Acrylamide

Product 1

HCID 6539894HCID 6539894, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred suspension of (E)-3-(6-aminopyridin-3-yl)-N-methyl-N-[(1-methyl-1H-indol-2-yl)methyl]acrylamide (0.50 g, 1.56 mmole) and NaHCO3 (0.51 g, 6.09 mmole) in THF (75 mL) was added acetic anhydride (0.38 g, 3.74 mmole). The reaction was heated at reflux for 24 hrs and then concentrated. The remaining residue was extracted with EtOAc and purified on silica gel (95:5 CHCl3/CH3OH) to give the title compound (0.54 g, 96%) as an off-white solid: MS (ES) m/e 363 (M+H)+.

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 24 hrs
  3. concentrationconcentrated
  4. extractionThe remaining residue was extracted with EtOAc
  5. custompurified on silica gel (95:5 CHCl3/CH3OH)

Sources & evidence

ORD record
ord-2fc55f2e68ed4120a8c0f496906fcc3c
Source dataset
uspto-grants-2012_05
Patent number
US08173646B2

Reaction notes

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