HCID 22914668, compound → HCID 22914700, compound

HRID 1377721Notes

Reaction equation

HRID 1377721 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([CH2:21][C:22]([N:24]3[CH2:29][CH2:28][CH:27]([N:30]4[C:39]5[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=5)[CH2:33][CH2:32][C:31]4=[O:40])[CH2:26][CH2:25]3)=[O:23])=[C:17]([O:41][CH3:42])[CH:16]=2)[CH2:10][CH2:9]1)=O)(C)(C)C>C(OCC)(=O)C>[NH:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([CH2:21][C:22]([N:24]3[CH2:25][CH2:26][CH:27]([N:30]4[C:39]5[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=5)[CH2:33][CH2:32][C:31]4=[O:40])[CH2:28][CH2:29]3)=[O:23])=[C:17]([O:41][CH3:42])[CH:16]=2)[CH2:10][CH2:9]1

Participants

3

Reactant 1

HCID 22914668HCID 22914668, compound

Product 1

HCID 22914700HCID 22914700, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To 250 mL of dry ethyl acetate under N2 was added 1-(1-(4-(N-tert-Butyloxycarbonyl-4-piperidinyloxy)-2-methoxyphenylacetyl)-piperidin-4-yl)-3,4-dihydro-2(1H)-quinolinone (1.2 g, 2 mmol) from Example 194, and the solution was cooled to 0° C. in an ice-water bath. Anhydrous HCl gas was bubbled into the solution at 0° C. for 30 min. The solution was stirred for an additional 30 min at 0° C. then the ice bath was removed and N2 was bubbled through the solution to remove the excess HCl. Addition of hexane caused precipitation of the HCl salt. The solid was dried in vacuo to remove solvent and then was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate. The organic layer was washed with water and brine and was dried over anhydrous MgSO4. The solvent was removed under reduced pressure. The residue was dissolved in methylene chloride and the solvent was removed under reduced pressure to give the title compound as an amorphous solid.

Workup

  1. customAnhydrous HCl gas was bubbled into the solution at 0° C. for 30 min
  2. customthe ice bath was removed
  3. customN2 was bubbled through the solution
  4. customto remove the excess HCl
  5. additionAddition of hexane
  6. customprecipitation of the HCl salt
  7. customThe solid was dried in vacuo
  8. customto remove solvent
  9. customwas partitioned between ethyl acetate and saturated aqueous sodium bicarbonate
  10. washThe organic layer was washed with water and brine
  11. dry with materialwas dried over anhydrous MgSO4
  12. customThe solvent was removed under reduced pressure
  13. dissolutionThe residue was dissolved in methylene chloride
  14. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-1f69c6af869747e08c8d7503bb7304e1
Source dataset
uspto-grants-1997_09
Patent number
US05665719

Reaction notes

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