Potassium Carbonate → HCID 178486052, compound

HRID 1366760Notes

Reaction equation

[OH: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:16])([O-])[O-:14].[K+].[K+].C(OC([CH2:26][NH:27][C@@H:28]1[CH2:33][CH2:32][C@H:31](OS(C)(=O)=O)[CH2:30][CH2:29]1)=O)(C)(C)C>CN(C=O)C>[C:4]([O:14][C:13](=[O:16])[N:27]([CH3:26])[C@H:28]1[CH2:29][CH2:30][C@H:31]([O: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)[CH2:32][CH2:33]1)([CH3:9])([CH3:5])[CH3:3]

Participants

Conditions

Temperature: 110 °C

Procedure

suspension of 6-Hydroxy-2H-isoquinolin-1-one (410 mg, 2.52 mmol) and potassium carbonate (420 mg, 3.03 mmol) in DMF (7 ml) was heated to 110° C. and a solution of methanesulfonic acid cis-4-(tert-butoxycarbonylmethylamino)cyclohexyl ester (930 mg, 3.03 mmol) in DMF (3 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 aqueous sodium hydrogen carbonate. The organics were collected through a hydrophobic frit and concentrated to afford crude product. The residue was purified by flash chromatography on silica (eluent: dichloromethane followed by 2M ammonia in methanol) to give trans-methyl[4-(1-oxo-1,2-dihydroisoquinolin-6-yloxy)cyclohexyl]carbamic acid tert-butyl ester (400 mg, 42%), EI-MS: m/z=373.1 [M+H]+.

Workup

temperatureHeating
customthe solvent removed in vacuo
washwashed with aqueous sodium hydrogen carbonate
customThe organics were collected through a hydrophobic frit
concentrationconcentrated
customto afford crude product
customThe residue was purified by flash chromatography on silica (eluent: dichloromethane followed by 2M ammonia in methanol)

Sources & evidence

ORD record: ord-bf91b1332a634a16817936bf9227d91d
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07893088B2

Reaction notes

Loading…