Acetic Anhydride → HCID 22914738, compound

HRID 1377718Notes

Reaction equation

HRID 1377718 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([O:7][C:8]2[CH:32]=[CH:31][C:11]([C:12]([N:14]3[CH2:19][CH2:18][CH:17]([N:20]4[C:29]5[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=5)[CH2:23][CH2:22][C:21]4=[O:30])[CH2:16][CH2:15]3)=[O:13])=[C:10]([O:33][CH3:34])[CH:9]=2)[CH2:3][CH2:2]1.[C:35](OC(=O)C)(=[O:37])[CH3:36].CCN(C(C)C)C(C)C>C(Cl)Cl>[C:35]([N:1]1[CH2:6][CH2:5][CH:4]([O:7][C:8]2[CH:32]=[CH:31][C:11]([C:12]([N:14]3[CH2:15][CH2:16][CH:17]([N:20]4[C:29]5[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=5)[CH2:23][CH2:22][C:21]4=[O:30])[CH2:18][CH2:19]3)=[O:13])=[C:10]([O:33][CH3:34])[CH:9]=2)[CH2:3][CH2:2]1)(=[O:37])[CH3:36]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 81531DiisopropylethylamineHCID 22914659HCID 22914659, compound

Product 1

HCID 22914738HCID 22914738, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(1-(4-(4-piperidinyloxy)-2-methoxybenzoyl)piperidin-4-yl)-3,4-dihydro-2(1H)-quinolinone (150 mg, 0.27 mmol) from Example 190 in methylene chloride (10 mL) was added acetic anhydride (0.050 mL, 0.54 mmol) and DIEA (0.050 mL, 0.27 mmol) and the reaction was stirred at ambient temperature for 2 hours. The solvent was removed under reduced pressure and the residue was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate. The organic layer was washed with water (2×) and brine, and was dried over anhydrous MgSO4. The solvent was removed under reduced pressure to give the title compound as an amorphous solid.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate
  3. washThe organic layer was washed with water (2×) and brine
  4. dry with materialwas dried over anhydrous MgSO4
  5. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-ff7b66740c394d6a81f8e3cadb68dd7c
Source dataset
uspto-grants-1997_09
Patent number
US05665719

Reaction notes

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