Methanesulfonyl chloride → (+/-)-6-Methoxy-2-methyl-3-[1-(methylsulfonyl)piperidin-3-yl]-4-phenylisoquinolin-1(2H)-one
Reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[N:8]([CH3:14])[C:7]([CH:15]1[CH2:20][CH2:19][CH2:18][NH:17][CH2:16]1)=[C:6]2[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(N(CC)C(C)C)(C)C.[CH3:36][S:37](Cl)(=[O:39])=[O:38].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[N:8]([CH3:14])[C:7]([CH:15]1[CH2:20][CH2:19][CH2:18][N:17]([S:37]([CH3:36])(=[O:39])=[O:38])[CH2:16]1)=[C:6]2[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a methylene chloride (0.100 mL) solution of (±)-6-methoxy-2-methyl-4-phenyl-3-piperidin-3-ylisoquinolin-1(2H)-one (30 mg, 0.086 mmol) and N,N-diisopropylethylamine (0.017 mL, 0.095 mmol) was added methanesulfonyl chloride (0.007 mL, 0.095 mmol). After 24 hours saturated sodium bicarbonate and additional methylene chloride were added. The layers were separated and the organic phase dried with anhydrous magnesium sulfate. Evaporation of the solvent in vacuo followed by trituration with ether-EtOAc gave a white solid which was isolated by vacuum filtration to give the titled product. ESI+MS: 427.1 [M+H]+.
Workup
- customThe layers were separated
- dry with materialthe organic phase dried with anhydrous magnesium sulfate
- customEvaporation of the solvent in vacuo
- customgave a white solid which
- customwas isolated by vacuum filtration
Sources & evidence
- ORD record
- ord-6c3f74d63301475dbdfd131f9419fa5c
- Source dataset
- uspto-grants-2010_06
- Patent number
- US07741322B2
Reaction notes
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