Pyridine → HCID 49834173, compound

HRID 1947644Notes

Reaction equation

[Cl:1][C:2]1[CH:24]=[CH:23][C:5]([CH2:6][NH:7][C:8]2[CH:17]=[C:16]3[C:11]([C:12]([CH3:22])([CH3:21])[CH2:13][N:14]([CH2:19][CH3:20])[C:15]3=[O:18])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.N1C=CC=CC=1.[CH3:31][N:32]1[CH:36]=[C:35]([S:37](Cl)(=[O:39])=[O:38])[N:34]=[CH:33]1>C(#N)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]([C:8]2[CH:17]=[C:16]3[C:11]([C:12]([CH3:21])([CH3:22])[CH2:13][N:14]([CH2:19][CH3:20])[C:15]3=[O:18])=[CH:10][CH:9]=2)[S:37]([C:35]2[N:34]=[CH:33][N:32]([CH3:31])[CH:36]=2)(=[O:39])=[O:38])=[CH:23][CH:24]=1

Participants

Conditions

Temperature: 150 °C

Procedure

To a stirred solution of 7-(4-chloro-benzylamino)-2-ethyl-4,4-dimethyl-3,4-dihydro-2H-isoquinolin-1-one (17 mg, 0.05 mmol) and pyridine (9 μl, 0.11 mmol) in anhydrous acetonitrile (1 ml) was added 1-methyl-1H-imidazole-4-sulfonyl chloride (20 mg, 0.11 mmol) and the reaction heated to 150° C. in a microwave for 0.5 hrs. The solvent was evaporated in vacuo and the crude residue purified by preparative tlc (5% methanol in dichloromethane) to afford the title compound as a colourless solid (5 mg, 21%). HPLC retention time 4.42 min. Mass spectrum (ES+) m/z 487 (M+H).

Workup

customThe solvent was evaporated in vacuo
customthe crude residue purified by preparative tlc (5% methanol in dichloromethane)

Sources & evidence

ORD record: ord-fd008832905c4ccf8948fce4cd92d6ea
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08399481B2

Reaction notes

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