Ethanesulfonylchloride, 2-chloro- → HCID 22914660, compound

HRID 1377719Notes

Reaction equation

HRID 1377719 reaction equation
Cl[CH2:2][CH2:3][S:4](Cl)(=[O:6])=[O:5].[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[CH2:26][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.CCN(C(C)C)C(C)C.S(Cl)(Cl)(=O)=O>C(Cl)Cl>[CH:3]([S:4]([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[CH2:22][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)(=[O:6])=[O:5])=[CH2:2]

Participants

6

Reactant 4

HCID 15385Ethanesulfonylchloride, 2-chloro-HCID 24648Sulfuryl chlorideHCID 81531DiisopropylethylamineHCID 22914659HCID 22914659, compound

Product 1

HCID 22914660HCID 22914660, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a 25 mL flask containing 3 mL of methylene chloride was added 2-chloro-1-ethanesulfonyl chloride (0.046 mL, 0.44 mmol) and the solution was cooled to 0° C. under N2. To a 10 mL addition funnel containing 8 mL of methylene chloride was added 1-(1-(4-(4-piperidinyloxy)-2-methoxybenzoyl)piperidin-4-yl)-3,4-dihydro-2(1H)-quinolinone (200 mg, 0.4 mmol) from Example 190 and DIEA (0.35 mL, 2.0 mmol). This solution was added slowly over 15 min to the cold, stirred solution of sulfonyl chloride. The reaction mixture was stirred at 0° C. for 30 min and then at ambient temperature for 16 hrs. The solvent was removed under reduced pressure and the residue was partitioned between ethyl acetate and water. The layers were separated and aqueous phase was extracted with ethyl acetate (3×). The combined organic phases were dried over MgSO4 and filtered. The solvent was removed under reduced pressure and the residue purified by pressurized silica gel column chromatography using 95:5 CH2Cl2 :MeOH as eluant. The product-containing fractions were combined and the solvent was removed under reduced pressure to give the title compound as an amorphous solid.

Workup

  1. additionTo a 10 mL addition funnel
  2. additionThis solution was added slowly over 15 min to the cold
  3. waitat ambient temperature for 16 hrs
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was partitioned between ethyl acetate and water
  6. customThe layers were separated
  7. extractionaqueous phase was extracted with ethyl acetate (3×)
  8. dry with materialThe combined organic phases were dried over MgSO4
  9. filtrationfiltered
  10. customThe solvent was removed under reduced pressure
  11. customthe residue purified by pressurized silica gel column chromatography
  12. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-ebe683f0ccc9439e9086d83e4f56f1fd
Source dataset
uspto-grants-1997_09
Patent number
US05665719

Reaction notes

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