Potassium Carbonate → HCID 68808773, compound

HRID 2217900Notes

Reaction equation

HRID 2217900 reaction equation
[SH:1][CH:2](O)C.[Cl:5][C:6]1[C:7]([NH:26][C:27](=[O:35])[CH2:28][CH:29]2[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]2)=[C:8]2[C:13](=[CH:14][CH:15]=1)[N:12]=[C:11]([N:16]1[CH2:20][CH2:19][C@H:18](OS(C)(=O)=O)[CH2:17]1)[CH:10]=[CH:9]2.[C:36](=[O:39])([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:5][C:6]1[C:7]([NH:26][C:27](=[O:35])[CH2:28][CH:29]2[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]2)=[C:8]2[C:13](=[CH:14][CH:15]=1)[N:12]=[C:11]([N:16]1[CH2:20][CH2:19][C@H:18]([S:1][CH2:2][CH2:36][OH:39])[CH2:17]1)[CH:10]=[CH:9]2

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 4713212Mercapto-ethanolHCID 86609739N-[6-Chloro-2-[(3S)-3-[(methylsulfonyl)oxy]-1-pyrrolidinyl]-5-quinolinyl]-cyclohexaneacetamide

Product 1

HCID 68808773HCID 68808773, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

Mercaptoethanol (0.073 mL) was added to N-[6-chloro-2-[(3S)-3-[(methylsulfonyl)oxy]-1-pyrrolidinyl]-5-quinolinyl]-cyclohexaneacetamide (Example 33(a)) (0.1 g) and potassium carbonate (0.24 g) in dry N,N-dimethylformamide. The reaction mixture was heated at 60° C. in a microwave for 2 hours and then partitioned between water and ethyl acetate. The combined organics were washed with brine, dried and concentrated. Purification (SiO2, methanol:dichloromethane 3:97 as eluant) gave the sub-titled compound as a solid (0.05 g).

Workup

  1. custompartitioned between water and ethyl acetate
  2. washThe combined organics were washed with brine
  3. customdried
  4. concentrationconcentrated
  5. customPurification (SiO2, methanol:dichloromethane 3:97 as eluant)

Sources & evidence

ORD record
ord-c91fc0eae2514e0cab2a5731f581fcf3
Source dataset
uspto-grants-2008_08
Patent number
US07408065B2

Reaction notes

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