Acetic Anhydride → HCID 11403155, compound

HRID 1351082Notes

Reaction equation

HRID 1351082 reaction equation
[CH:1]1[C:6]2[C:7]3[O:8][C:9]4[C:14]([C:15]=3[NH:16][C:17](=[O:18])[C:5]=2[CH:4]=[CH:3][CH:2]=1)=[CH:13][CH:12]=[CH:11][CH:10]=4.[C:19](OC(=O)C)(=[O:21])[CH3:20]>N1C=CC=CC=1>[CH:1]1[C:6]2=[C:7]3[C:15](=[N:16][C:17]([O:18][C:19](=[O:21])[CH3:20])=[C:5]2[CH:4]=[CH:3][CH:2]=1)[C:14]1[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=1)[O:8]3

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 10014294HCID 10014294, compound

Product 1

HCID 11403155HCID 11403155, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of compound 15c (500 mg, 2.13 mmol) in pyridine (10 mL) was added acetic anhydride (4 mL). The resultant mixture was heated at 100° C. for 9 h, then cooled slowly to room temperature overnight. The solvent was removed on the rotary evaporator and the residual oil was extracted into 50 mL ethyl acetate. The organic layer was washed with 50 mL of 1 N aqueous hydrochloric acid, dried (sodium sulfate), and the solvent removed in vacuo to provide 308 mg (52% yield) of compound 16g as a white powder.

Workup

  1. customThe solvent was removed on the rotary evaporator
  2. extractionthe residual oil was extracted into 50 mL ethyl acetate
  3. washThe organic layer was washed with 50 mL of 1 N aqueous hydrochloric acid
  4. dry with materialdried (sodium sulfate)
  5. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-72c6a927c2c24e6a8e79c0b2c19fb4a0
Source dataset
uspto-grants-2007_05
Patent number
US07217709B2

Reaction notes

Loading…