HCID 22914704, compound → HCID 22914659, compound

HRID 1377717Notes

Reaction equation

HRID 1377717 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:39]=[CH:38][C:18]([C:19]([N:21]3[CH2:26][CH2:25][CH:24]([N:27]4[C:36]5[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=5)[CH2:30][CH2:29][C:28]4=[O:37])[CH2:23][CH2:22]3)=[O:20])=[C:17]([O:40][CH3:41])[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:39]=[CH:38][C:18]([C:19]([N:21]3[CH2:22][CH2:23][CH:24]([N:27]4[C:36]5[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=5)[CH2:30][CH2:29][C:28]4=[O:37])[CH2:25][CH2:26]3)=[O:20])=[C:17]([O:40][CH3:41])[CH:16]=2)[CH2:10][CH2:9]1

Participants

3

Reactant 1

HCID 22914704HCID 22914704, compound

Product 1

HCID 22914659HCID 22914659, 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-t-Butoxycarbonyl-4-piperidinyloxy)-2-methoxybenzoyl)piperidin-4-yl)-3,4-dihydro-2(1H)-quinolinone (1.5 gm, 2.65 mmol) from Example 189 and the solution was cooled to 0° C. in an ice-water bath. Anhydrous HCl gas was bubbled into the solution at 0° C. until for 30 min. The saturated solution was stirred for an additional 30 min at 0° C. then the ice bath was removed and N2 was bubbled through the mixture to remove 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 (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. customAnhydrous HCl gas was bubbled into the solution at 0° C. until for 30 min
  2. customthe ice bath was removed
  3. customN2 was bubbled through the mixture
  4. customto remove 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 (2×) and brine
  11. dry with materialwas dried over anhydrous MgSO4
  12. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-a37abad5393d451c897430e740646811
Source dataset
uspto-grants-1997_09
Patent number
US05665719

Reaction notes

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