Acetic Anhydride → HCID 18700154, compound

HRID 2289360Notes

Reaction equation

HRID 2289360 reaction equation
Cl.[F:2][C:3]([F:41])([F:40])[CH2:4][O:5][C:6]1[CH:11]=[C:10]([O:12][CH:13]2[CH2:18][CH2:17][CH:16]([NH2:19])[CH2:15][CH2:14]2)[CH:9]=[CH:8][C:7]=1[CH2:20][C:21]([N:23]1[CH2:28][CH2:27][CH:26]([N:29]2[C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=3[CH2:32][O:31][C:30]2=[O:39])[CH2:25][CH2:24]1)=[O:22].[C:42](OC(=O)C)(=[O:44])[CH3:43].CCN(C(C)C)C(C)C>C(Cl)Cl>[F:41][C:3]([F:2])([F:40])[CH2:4][O:5][C:6]1[CH:11]=[C:10]([O:12][CH:13]2[CH2:14][CH2:15][CH:16]([NH:19][C:42](=[O:44])[CH3:43])[CH2:17][CH2:18]2)[CH:9]=[CH:8][C:7]=1[CH2:20][C:21]([N:23]1[CH2:28][CH2:27][CH:26]([N:29]2[C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=3[CH2:32][O:31][C:30]2=[O:39])[CH2:25][CH2:24]1)=[O:22]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 81531DiisopropylethylamineHCID 18700118HCID 18700118, compound

Product 1

HCID 18700154HCID 18700154, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(1-(2-(2,2,2-trifluoroethoxy)-4-(1-aminocyclohex-4-yl oxy)phenylacetyl)piperidin-4-yl)-4H-3,1-benzoxazin-2(1H)-one hydrochloride (0.090 g, 0.15 mmol) from Example 41 in CH2Cl2 (4 mL) was added acetic anhydride (0.031 mL, 0.3 mmol) and DIEA (0.052 mL, 0.3 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 (50 mL) and washed with 0.25 M aqueous citric acid (20 mL), H2O (10 mL), and saturated aqueous NaHCO3 (20 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 (50 mL)
  3. washwashed with 0.25 M aqueous citric acid (20 mL), H2O (10 mL), and saturated aqueous NaHCO3 (20 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-893ef2121099446fbcd07656c54c4659
Source dataset
uspto-grants-2000_07
Patent number
US06090805

Reaction notes

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