Acetic Anhydride → HCID 18700090, compound

HRID 2289358Notes

Reaction equation

HRID 2289358 reaction equation
Cl.[NH:2]1[CH2:7][CH2:6][CH:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][C:16]([N:18]3[CH2:23][CH2:22][CH:21]([N:24]4[C:29]5[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=5[CH2:27][O:26][C:25]4=[O:34])[CH2:20][CH2:19]3)=[O:17])=[C:11]([O:35][C:36]([F:39])([F:38])[F:37])[CH:10]=2)[CH2:4][CH2:3]1.[C:40](OC(=O)C)(=[O:42])[CH3:41].CCN(C(C)C)C(C)C>C(Cl)Cl>[F:38][C:36]([F:39])([F:37])[O:35][C:11]1[CH:10]=[C:9]([O:8][CH:5]2[CH2:4][CH2:3][N:2]([C:40](=[O:42])[CH3:41])[CH2:7][CH2:6]2)[CH:14]=[CH:13][C:12]=1[CH2:15][C:16]([N:18]1[CH2:23][CH2:22][CH:21]([N:24]2[C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=3[CH2:27][O:26][C:25]2=[O:34])[CH2:20][CH2:19]1)=[O:17]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 81531DiisopropylethylamineHCID 18700134HCID 18700134, compound

Product 1

HCID 18700090HCID 18700090, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(1-(4-(4-piperidinyloxy)-2-(trifluoromethoxy)-phenylacetyl)piperidin-4-yl)-4H-3,1-benzoxazin-2(1H)-one hydrochloride (0.45 g, 0.77 mmol) from Example 39 in CH2Cl2 (50 mL) was added acetic anhydride (0.15 mL, 1.5 mmol) and DIEA (0.26 mL, 1.5 mmol). The solution was stirred at ambient temperature for 1 h and the solvent was removed under reduced pressure. The residue was dissolved in EtOAc (100 mL) and washed with 0.25 M aqueous citric acid (50 mL), H2O (25 mL), and saturated aqueous NaHCO3 (75 mL). The organic phase was dried (MgSO4), filtered, and 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. dissolutionThe residue was dissolved in EtOAc (100 mL)
  3. washwashed with 0.25 M aqueous citric acid (50 mL), H2O (25 mL), and saturated aqueous NaHCO3 (75 mL)
  4. dry with materialThe organic phase was dried (MgSO4)
  5. filtrationfiltered
  6. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-5ae2b967a8444d4cb7cd6b2f77bf54a4
Source dataset
uspto-grants-2000_07
Patent number
US06090805

Reaction notes

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