Acetic Anhydride → HCID 9958479, compound

HRID 1956000Notes

Reaction equation

HRID 1956000 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([O:7][C:8]2[C:32]([F:33])=[CH:31][C:11]([C:12]([N:14]3[CH2:19][CH2:18][CH:17]([N:20]4[C:25]5[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=5[CH2:23][O:22][C:21]4=[O:30])[CH2:16][CH2:15]3)=[O:13])=[C:10]([O:34][CH3:35])[CH:9]=2)[CH2:3][CH2:2]1.[C:36](OC(=O)C)(=[O:38])[CH3:37].CCN(C(C)C)C(C)C>C(Cl)Cl>[C:36]([N:1]1[CH2:6][CH2:5][CH:4]([O:7][C:8]2[C:32]([F:33])=[CH:31][C:11]([C:12]([N:14]3[CH2:15][CH2:16][CH:17]([N:20]4[C:25]5[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=5[CH2:23][O:22][C:21]4=[O:30])[CH2:18][CH2:19]3)=[O:13])=[C:10]([O:34][CH3:35])[CH:9]=2)[CH2:3][CH2:2]1)(=[O:38])[CH3:37]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 81531DiisopropylethylamineHCID 10505002HCID 10505002, compound

Product 1

HCID 9958479HCID 9958479, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 1-(1-(4-(4-piperidinyloxy)-5-fluoro-2-methoxybenzoyl)piperidin-4-yl)-4H-3,1-benzoxazin-2(1H)-one of Example 16 (200 mg, 0.41 mmol) in DCM (5 mL) at ambient temperature was added acetic anhydride (77 mg, 0.75 mmol) and DIEA (0.17 mL, 1.0 mmol). The solution was stirred at ambient temperature for 24 h, diluted with DCM (20 mL), washed with saturated aqueous NaHCO3 (50 mL), dried (MgSO4), and filtered. The solvent was removed under reduced pressure and the residue was purified by pressurized silica gel column chromatography using a gradient elution of 2-5% MeOH-DCM. 1-(1-(4-(N-acetyl-4-piperidinyloxy)-5-fluoro-2-methoxybenzoyl)piperidin-4-yl) -4H-3,1-benzoxazin-2(1H)-one was obtained as an amorphous solid.

Workup

  1. washwashed with saturated aqueous NaHCO3 (50 mL)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was purified by pressurized silica gel column chromatography
  6. washa gradient elution of 2-5% MeOH-DCM

Sources & evidence

ORD record
ord-9b5fd5d6e3df4a2bb16ffb66e033058e
Source dataset
uspto-grants-1998_07
Patent number
US05777123

Reaction notes

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