2-Hydrazinylpyridine-4-carbonitrile → HCID 86725502, compound

HRID 514366Notes

Reaction equation

[C:1]([O:4][C:5]1[CH:10]=[C:9]([C:11](=O)/[CH:12]=[CH:13]/[N:14](C)C)[CH:8]=[CH:7][C:6]=1[S:18]([CH3:21])(=[O:20])=[O:19])(=O)C.[NH:22]([C:24]1[CH:25]=[C:26]([CH:29]=[CH:30][N:31]=1)[C:27]#[N:28])N>CCO.CC(O)=O>[CH3:1][O:4][C:5]1[CH:10]=[C:9]([C:11]2[N:22]([C:24]3[CH:25]=[C:26]([C:27]#[N:28])[CH:29]=[CH:30][N:31]=3)[N:14]=[CH:13][CH:12]=2)[CH:8]=[CH:7][C:6]=1[S:18]([CH3:21])(=[O:20])=[O:19]

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 5-[(2E)-3-(dimethylamino)prop-2-enoyl]-2-(methylsulfonyl)phenyl acetate (1.5 g, 5.3 mmol) and 2-hydrazinylisonicotinonitrile (0.8 g, 6 mmol, PREPARATION 2) in EtOH (15 mL) and AcOH (3 mL) was stirred at 90° C. overnight. The reaction mixture was cooled, concentrated, and purified by prep-HPLC to afford the title compound (270 mg, 14%). 1H NMR (400 MHz, CDCl3): δ 3.26 (3H, s), 3.96 (3H, s), 6.58 (1H, d, J=1.6 Hz), 6.96 (1H, dd, J=8.4, 1.2 Hz), 7.05 (1H, d, J=1.2 Hz), 7.41 (1H, dd, J=4.8, 1.2 Hz), 7.81 (1H, d, J=2.0 Hz), 7.93 (1H, d, J=8.4 Hz), 8.18 (1H, s), 8.35 (1H, d, J=4.8 Hz). [M+H] Calc'd for C17H14N4O3S, 355. Found, 355.

Workup

temperatureThe reaction mixture was cooled
concentrationconcentrated
custompurified by prep-HPLC

Sources & evidence

ORD record: ord-392eb85b9dd547c3bee7d13cba520b2e
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09107916B2

Reaction notes

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