Acetic Anhydride → HCID 59140179, compound

HRID 2064009Notes

Reaction equation

HRID 2064009 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:10]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([Si:18]([CH3:21])([CH3:20])[CH3:19])=[CH:14][C:13]=2[F:22])=[N:9][C:8]([CH2:23][NH2:24])=[CH:7][N:6]=1)=[O:4].[C:25](OC(=O)C)(=[O:27])C>C(O)=O>[CH3:1][O:2][C:3]([C:5]1[C:10]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([Si:18]([CH3:19])([CH3:20])[CH3:21])=[CH:14][C:13]=2[F:22])=[N:9][C:8]([CH2:23][NH:24][CH:25]=[O:27])=[CH:7][N:6]=1)=[O:4]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 591401895-Aminomethyl-3-(2-fluoro-4-trimethylsilanyl-phenylamino)-pyrazine-2-carboxylic acid methyl ester

Product 1

HCID 59140179HCID 59140179, compoundYield 98.3%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A solution of 5-aminomethyl-3-(2-fluoro-4-trimethylsilanyl-phenylamino)-pyrazine-2-carboxylic acid methyl ester (800 mg, 2.30 mmol) from above in formic acid (12 mL) and acetic anhydride (4 mL) was stirred at ambient temperature under N2 for 1.5 hour. The reaction mixture was concentrated in vacuo, and the residue was azeotroped with toluene. The resultant residue was diluted with ethyl acetate. The organic layer was washed with saturated aqueous solution of sodium bicarbonate, water and brine, dried (Na2SO4), filtered and concentrated in vacuo to afford the title compound as a yellow foam (850 mg, 98.3%). LCMS (method D1: RT=1.09 min, [M+H]+=377.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue was azeotroped with toluene
  3. additionThe resultant residue was diluted with ethyl acetate
  4. washThe organic layer was washed with saturated aqueous solution of sodium bicarbonate, water and brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cac9b57d7f4d4003a76e31dd88fd9cb9
Source dataset
uspto-grants-2012_10
Patent number
US08288408B2

Reaction notes

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