Chlorosuccinimide → 3-({[(1R)-1-(5-fluoro-2-pyridinyl)ethyl]amino}carbonyl)-N-hydroxy-5-(5-methyl-2-pyridinyl)benzenecarboximidoyl chloride

HRID 1257544Notes

Reaction equation

[F:1][C:2]1[CH:3]=[CH:4][C:5]([C@H:8]([NH:10][C:11](=[O:28])[C:12]2[CH:17]=[C:16]([C:18]3[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][N:19]=3)[CH:15]=[C:14](/[CH:25]=[N:26]/[OH:27])[CH:13]=2)[CH3:9])=[N:6][CH:7]=1.[Cl:29]N1C(=O)CCC1=O>O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C@H:8]([NH:10][C:11]([C:12]2[CH:13]=[C:14]([C:25]([Cl:29])=[N:26][OH:27])[CH:15]=[C:16]([C:18]3[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][N:19]=3)[CH:17]=2)=[O:28])[CH3:9])=[N:6][CH:7]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of N-[(1R)-1-(5-fluoro-2-pyridinyl)ethyl]-3-[(E)-(hydroxyimino)methyl]-5-(5-methyl-2-pyridinyl)benzamide (0.703 g, 1.86 mmol) N,N-dimethylformamide (1.9 mL) was added N-chlorosuccinimide (0.260 g, 1.95 mmol). The reaction mixture was stirred at 50° C. for 1 h. The temperature was raised to 70° C. for 1 h. The mixture was cooled to ambient temperature. Water was added. The mixture was extracted with diethyl ether (3×). The combined organic extracts were washed with water (3×), dried over magnesium sulfate, filtered and concentrated to give the title compound (0.795 g) MS 413.0 (M+1).

Workup

temperatureThe temperature was raised to 70° C. for 1 h
temperatureThe mixture was cooled to ambient temperature
extractionThe mixture was extracted with diethyl ether (3×)
washThe combined organic extracts were washed with water (3×)
dry with materialdried over magnesium sulfate
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-fb9f2ac36cde4bbe95ec5fe6cafb0db8
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08461185B2

Reaction notes

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