6-hydrazinyl-N,N-dimethylpyridine-3-sulfonamide → N,N-dimethyl-6-[3-methyl-5-oxo-4-(pyridin-3-ylmethyl)-2,5-dihydro-1H-pyrazol-1-yl]pyridine-3-sulfonamide

HRID 45224Notes

Reaction equation

[NH:1]([C:3]1[N:8]=[CH:7][C:6]([S:9]([N:12]([CH3:14])[CH3:13])(=[O:11])=[O:10])=[CH:5][CH:4]=1)[NH2:2].O=[C:16]([CH3:29])[CH:17]([CH2:22][C:23]1[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=1)[C:18](OC)=[O:19]>CCO.CC(O)=O.CCOC(C)=O>[CH3:13][N:12]([CH3:14])[S:9]([C:6]1[CH:7]=[N:8][C:3]([N:1]2[C:18](=[O:19])[C:17]([CH2:22][C:23]3[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=3)=[C:16]([CH3:29])[NH:2]2)=[CH:4][CH:5]=1)(=[O:10])=[O:11]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 400 mg (1.85 mmol) of 6-hydrazino-N,N-dimethylpyridine-3-sulfonamide and 383 mg (1.85 mmol) of methyl 3-oxo-2-(pyridin-3-ylmethyl)butanoate in 4 mL of EtOH/AcOH mixture (1:1) is heated for 4 hours at 80° C. and then concentrated under reduced pressure. The residue obtained is taken up in 20 mL of EtOAc, washed successively with water (2×20 mL), saturated NaHCO3 solution (20 mL) and brine (20 mL), dried over Na2SO4, filtered and concentrated under reduced pressure. The residue is then solidified in 20 mL of an Et2O/pentane mixture (1/1), filtered and recrystallized from a cyclohexane/EtOH mixture. 188 mg of N,N-dimethyl-6-[3-methyl-5-oxo-4-(pyridin-3-ylmethyl)-2,5-dihydro-1H-pyrazol-1-yl]pyridine-3-sulfonamide are obtained in the form of white crystals.

Workup

concentrationconcentrated under reduced pressure
customThe residue obtained
washwashed successively with water (2×20 mL), saturated NaHCO3 solution (20 mL) and brine (20 mL)
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated under reduced pressure
filtrationfiltered
customrecrystallized from a cyclohexane/EtOH mixture

Sources & evidence

ORD record: ord-fdc12b19814d477786c6489b82fe52ce
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08541455B2

Reaction notes

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