1,1'-Oxalyldiimidazole → Tert-butyl 5-(6-cyano-2-(4-fluorophenyl)-1-oxo-1,2-dihydroisoquinolin-3-yl)pentanoate

HRID 927282Notes

Reaction equation

N1(C(=O)C(N2C=CN=C2)=O)C=CN=C1.[F:15][C:16]1[CH:21]=[CH:20][C:19]([N:22]2[C:31]([CH2:32][CH2:33][CH2:34][CH2:35][C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])=[CH:30][C:29]3[C:24](=[CH:25][CH:26]=[C:27]([CH:43]=[N:44]O)[CH:28]=3)[C:23]2=[O:46])=[CH:18][CH:17]=1>C1(C)C=CC=CC=1.ClCCCl.C(OCC)(=O)C>[C:43]([C:27]1[CH:28]=[C:29]2[C:24](=[CH:25][CH:26]=1)[C:23](=[O:46])[N:22]([C:19]1[CH:20]=[CH:21][C:16]([F:15])=[CH:17][CH:18]=1)[C:31]([CH2:32][CH2:33][CH2:34][CH2:35][C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])=[CH:30]2)#[N:44]

Participants

Conditions

Temperature: 80 °C

Procedure

1,2-di-(1H-imidazol-1-yl)ethane-1,2-dione (130 mg, 0.684 mmol) was added to a stirred, room temperature mixture of tert-butyl 5-(2-(4-fluorophenyl)-6-((hydroxyimino)methyl)-1-oxo-1,2-dihydroisoquinolin-3-yl)pentanoate (200 mg, 0.456 mmol) in toluene (6.00 mL) and 1,2-dichloroethane (2 mL) and the mixture was stirred at 80° C. for 2 h. The mixture was cooled, diluted with ethyl acetate (20 mL), washed with aqueous sodium hydrogen carbonate (1 M, 1×15 mL), dried (MgSO4), filtered and the solvent was evaporated under reduced pressure to give tert-butyl 5-(6-cyano-2-(4-fluorophenyl)-1-oxo-1,2-dihydroisoquinolin-3-yl)pentanoate (185 mg, 0.440 mmol) as a yellow gum.

Workup

temperatureThe mixture was cooled
washwashed with aqueous sodium hydrogen carbonate (1 M, 1×15 mL)
dry with materialdried (MgSO4)
filtrationfiltered
customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record: ord-6f713ce7c79849dc8ee207ee0c178ce5
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09290454B2

Reaction notes

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