Potassium Carbonate → HCID 68877258, compound

HRID 1435997Notes

Reaction equation

HRID 1435997 reaction equation
[SH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[NH:7][CH:6]=[CH:5]2.[C:13]([O:17][C:18]([N:20]1[CH2:25][CH2:24][CH:23](OS(C)(=O)=O)[CH2:22][CH2:21]1)=[O:19])([CH3:16])([CH3:15])[CH3:14].C([O-])([O-])=O.[K+].[K+].C(=O)([O-])O.[Na+]>CN(C)C=O.C(OCC)(=O)C.CCCCCCC>[C:13]([O:17][C:18]([N:20]1[CH2:25][CH2:24][CH:23]([S:1][C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[C:8](=[O:12])[NH:7][CH:6]=[CH:5]3)[CH2:22][CH2:21]1)=[O:19])([CH3:16])([CH3:14])[CH3:15]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 41848691-(tert-Butoxycarbonyl)-4-(methanesulfonyloxy)piperidineHCID 68874967HCID 68874967, compound

Product 1

HCID 68877258HCID 68877258, compoundYield 14.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 21899848Ethylacetate heptaneSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 6-mercapto-2H-isoquinolin-1-one (50 mg, 0.28 mmol), 4-methane-sulphonyloxy-piperidine-1-carboxylic acid tert-butyl ester (117 mg, 0.42 mmol) and K2CO3 (64 mg, 0.46 mmol) in N, N-dimethylformamide (1.5 ml) was heated at 50° C. then left at ambient temperature overnight. Saturated aqueous sodium hydrogen carbonate was added to the mixture which was extracted with ethyl acetate (x 3). The combined organics were dried (Na2SO4) and concentrated in vacuo to give a residue. Flash chromatography of the residue using ethyl acetate:heptane (1:9 to 99:1) gave 4-(1-Oxo-1,2-dihydroisoquinolin-6-ylsulfanyl)piperidine-1-carboxylic acid tert-butyl ester (15 mg). A dichloromethane:trifluoroacetic acetic acid solution (7:3, 5 ml) was added to the 4-(1-Oxo-1,2-dihydroisoquinolin-6-ylsulfanyl)piperidine-1-carboxylic acid tert-butyl ester and the mixture stirred for 2 h, then concentrated in vacuo to give a residue. The residue was loaded onto a pre-acidified SCX column using methanol and eluted with 2M ammonia in methanol to afford crude 6-(piperidin-4-ylsulfanyl)-2H-isoquinolin-1-one, which was purified by prep-HPLC (2 mg), El-MS: m/z=261.1 [M+H]+.

Workup

  1. extractionwas extracted with ethyl acetate (x 3)
  2. dry with materialThe combined organics were dried (Na2SO4)
  3. concentrationconcentrated in vacuo
  4. customto give a residue

Sources & evidence

ORD record
ord-01ffeca612694a7faa65b60d87e56bd3
Source dataset
uspto-grants-2009_11
Patent number
US07618985B2

Reaction notes

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