HCID 178454063, compound → HCID 178511695, compound
Reaction equation
C(OC(=O)[NH:7][C@H:8]1[CH2:13][CH2:12][C@@H:11]([O:14][C:15]2[CH:16]=[C:17]3[C:22](=[CH:23][CH:24]=2)[C:21](=[O:25])[NH:20][CH:19]=[CH:18]3)[CH2:10][CH2:9]1)(C)(C)C>ClCCl.FC(F)(F)C(O)=O>[NH2:7][C@@H:8]1[CH2:9][CH2:10][C@H:11]([O:14][C:15]2[CH:16]=[C:17]3[C:22](=[CH:23][CH:24]=2)[C:21](=[O:25])[NH:20][CH:19]=[CH:18]3)[CH2:12][CH2:13]1Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
A suspension of 6-Hydroxy-2H-isoquinolin-1-one (0.1 g, 0.62 mmol) and potassium carbonate (0.13 g, 0.93 mmol) in DMF (2.5 ml) was heated to 110° C. and a solution of methanesulfonic acid trans-4-tert-butoxycarbonylaminocyclohexyl ester (0.27 g, 0.93 mmol) in DMF (1.5 ml) was added dropwise. Heating was continued at 110° C. for 16 hours and the solvent removed in vacuo. The residue was taken up in chloroform/isopropanol (3:1) and washed with 1M NaOH. The organics were collected through a hydrophobic frit and concentrated to afford crude product. The residue was purified by prep-H PLC to give cis-[4-(1 -oxo-1,2-dihydroisoquinolin-6-yloxy)cyclohexyl]carbamic acid tert-butyl, EI-MS: m/z=359.1 [M+H]+. A mixture of the above cis-[4-(1-Oxo-1,2-dihydroisoquinolin-6-yloxy)cyclohexyl]carbamic acid tert-butyl ester in dichloromethane (0.9 ml) and trifluoroacetic acid (0.1 ml) was stirred at ambient temperature for 1 hour. The mixture was concentrated in vacuo then purified by ion exchange chromatography to give cis-6-(4-aminocyclohexyloxy)-2H-isoquinolin-1-one ( 3.1 mg), El-MS: m/z=259.1 [M+H]+.
Workup
- concentrationThe mixture was concentrated in vacuo
- customthen purified by ion exchange chromatography
Sources & evidence
- ORD record
- ord-d5774a68a8c343ae8d1f0228960c60ae
- Source dataset
- uspto-grants-2011_02
- Patent number
- US07893088B2
Reaction notes
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