Potassium Carbonate → HCID 69155507, compound

HRID 750352Notes

Reaction equation

HRID 750352 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[N:7]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([S:20]([NH2:23])(=[O:22])=[O:21])=[CH:16][CH:15]=1)[C:6]([C:24](=[O:27])[CH2:25][CH3:26])=[C:5]2[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C(=O)([O-])[O-].[K+].[K+].[N:40]1([C:46](Cl)=[O:47])[CH2:45][CH2:44][CH2:43][CH2:42][CH2:41]1>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[N:7]([CH2:13][C:14]1[CH:15]=[CH:16][C:17]([S:20]([NH:23][C:46]([N:40]3[CH2:45][CH2:44][CH2:43][CH2:42][CH2:41]3)=[O:47])(=[O:21])=[O:22])=[CH:18][CH:19]=1)[C:6]([C:24](=[O:27])[CH2:25][CH3:26])=[C:5]2[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2420851-Piperidinecarbonyl chlorideHCID 69156329HCID 69156329, compound

Product 1

HCID 69155507HCID 69155507, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 4-(6-bromo-1-oxo-4-phenyl-3-propionyl-1H-isoquinolin-2-ylmethyl)benzenesulfonamide (0.10 g), potassium carbonate (0.11 mg), 1-piperidinecarbonyl chloride (29 μl) and DMF (2.0 ml) was stirred at 50° C. for 18 hrs. After the completion of the reaction, the reaction mixture was concentrated, and the residue was diluted with dichloromethane. Then, this solution was washed with 1N hydrochloric acid, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by medium pressure preparative LC (hexane/ethyl acetate=4/1-1/1) to give the title compound (38 mg) as a colorless powder. HPLC analysis: purity 91.6% (retention time: 4.78 min). MS (ESI+): 636 (M+H), 638.

Workup

  1. customAfter the completion of the reaction
  2. concentrationthe reaction mixture was concentrated
  3. additionthe residue was diluted with dichloromethane
  4. washThen, this solution was washed with 1N hydrochloric acid
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by medium pressure preparative LC (hexane/ethyl acetate=4/1-1/1)

Sources & evidence

ORD record
ord-ee14e72163b64ed593c42992afb4e770
Source dataset
uspto-grants-2008_07
Patent number
US07402595B2

Reaction notes

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