Sodium Hydroxide → HCID 86710397, compound

HRID 1398409Notes

Reaction equation

C([O:5][C:6]([NH:8][C:9]1[N:10]=[CH:11][CH:12]=[C:13]2[C:18]=1[CH:17]=[N+:16]([CH3:19])[C:15]1[CH:20]=[C:21]([Cl:25])[C:22]([F:24])=[CH:23][C:14]2=1)=[O:7])(C)(C)C.[OH-].[Na+].[O-:28][Mn](=O)(=O)=O.[K+]>C(Cl)Cl.O>[Cl:25][C:21]1[C:22]([F:24])=[CH:23][C:14]2[C:13]3[C:18](=[C:9]([NH:8][C:6](=[O:7])[OH:5])[N:10]=[CH:11][CH:12]=3)[C:17](=[O:28])[N:16]([CH3:19])[C:15]=2[CH:20]=1

Participants

Conditions

Temperature: 90 °C

Procedure

To a stirred solution of 4-((tert-butoxycarbonyl)amino)-8-chloro-9-fluoro-6-methylbenzo[c][2,7]naphthyridin-6-ium (2.6 g, 2.310 mmol) in a mixture of DCM (10 mL) and water (50 mL) was added NaOH (0.370 g, 9.24 mmol) in three portions, followed by the addition of KMnO4 (1.461 g, 9.24 mmol) in five portions and the reaction was heated to 90° C. for 5 h. After cooling, the solvent was removed under reduced pressure. The residue was taken up in EtOAc (50 mL) and MeOH (50 mL) and stirred for 10 min. The reaction mixture was then passed through diatomaceous earth (Celite®), eluting with EtOAc. The filtrate was concentrated to yield (8-chloro-9-fluoro-6-methyl-5-oxo-5,6-dihydrobenzo[c][2,7]naphthyridin-4-yl)carbamic acid (2.35 g, 2.082 mmol, 90% crude yield) as a yellow solid which was taken to the next step without purification. LC/MS (ESI) m/e 322.1 [(M+H)+, calcd for C14H10ClFN3O3 322.0] LC/MS retention time (method E): tR=1.05 min.

Workup

temperatureAfter cooling
customthe solvent was removed under reduced pressure
washeluting with EtOAc
concentrationThe filtrate was concentrated

Sources & evidence

ORD record: ord-eb92465e677f49b0969c835632ba5bc4
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08901305B2

Reaction notes

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