Acetic Anhydride → HCID 25060792, compound

HRID 1673207Notes

Reaction equation

HRID 1673207 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]3[CH:25]([OH:26])[CH2:24][C:23]([CH3:28])([CH3:27])[O:22][C:11]3=[N:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=2[Cl:21])=[CH:4][CH:3]=1.[C:29](OC(=O)C)(=[O:31])[CH3:30]>N1C=CC=CC=1>[C:29]([O:26][CH:25]1[C:10]2[C:11](=[N:12][C:13]([C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=3[Cl:21])=[C:8]([C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=3)[CH:9]=2)[O:22][C:23]([CH3:28])([CH3:27])[CH2:24]1)(=[O:31])[CH3:30]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 25061041HCID 25061041, compound

Product 1

HCID 25060792HCID 25060792, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To the product of Example 68 (25 mg, 0.0575 mmol) was added acetic anhydride (0.25 mL, 2.65 mmol) in pyridine (2 mL). The reaction was stirred 4 h and was concentrated. The residue was diluted with EtOAc and washed with 1 M aq HCl followed by saturated aq NaHCO3/1 M aq NaOH (1:1). The solution was dried (Na2SO4). The concentrated residue was purified by flash chromatography on silica gel eluted with 50% EtOAc in hexane affording the title compound. (LC-2) HPLC/MS: 475.9 (M+1), 477.9 (M+3); Rt=4.29 min.

Workup

  1. concentrationwas concentrated
  2. additionThe residue was diluted with EtOAc
  3. washwashed with 1 M aq HCl
  4. dry with materialThe solution was dried (Na2SO4)
  5. customThe concentrated residue was purified by flash chromatography on silica gel
  6. washeluted with 50% EtOAc in hexane affording the title compound

Sources & evidence

ORD record
ord-532c626934d34fffb20d9629363d4c60
Source dataset
uspto-grants-2011_08
Patent number
US07999107B2

Reaction notes

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