Acetic Anhydride → HCID 57440852, compound

HRID 225932Notes

Reaction equation

HRID 225932 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[NH2:8][C:9]1[N:14]=[CH:13][C:12](/[CH:15]=[CH:16]/[C:17]([N:19]([CH2:21][C:22]2[C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[N:24]([CH3:31])[CH:23]=2)[CH3:20])=[O:18])=[CH:11][CH:10]=1.C(=O)(O)[O-].[Na+]>C1COCC1>[C:1]([NH:8][C:9]1[N:14]=[CH:13][C:12](/[CH:15]=[CH:16]/[C:17]([N:19]([CH3:20])[CH2:21][C:22]2[C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[N:24]([CH3:31])[CH:23]=2)=[O:18])=[CH:11][CH:10]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 9818527HCID 9818527, compound

Product 1

HCID 57440852HCID 57440852, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Acetic anhydride (0.12 mL, 1.24 mmole) was added to a solution of (E)-3-(6-aminopyridin-3-yl)-N-(1-methyl-1H-indol-3-ylmethyl)-N-methylacrylamide (0.10 g, 0.31 mmole) and sodium bicarbonate (0.13 g, 1.55 mmole) in THF (20 mL) at RT, and the reaction was heated at reflux under nitrogen. After 48 hr, the reaction was concentrated in vacuo and the residue was diluted with water and extracted with ethyl acetate. The combined extracts were dried over Na2SO4 and concentrated. Flash chromatography on silica gel (ethyl acetate) gave the title compound (50 mg, 45%) as a white solid: MS (ES) m/e 363 (M+H)+.

Workup

  1. temperaturethe reaction was heated
  2. temperatureat reflux under nitrogen
  3. concentrationthe reaction was concentrated in vacuo
  4. additionthe residue was diluted with water
  5. extractionextracted with ethyl acetate
  6. dry with materialThe combined extracts were dried over Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-02fff1ebe0b949ff8a9322c931ccd525
Source dataset
uspto-grants-2009_07
Patent number
US07557125B2

Reaction notes

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