2-Hydrazinopyridine → 5-Amino-1-(2-pyridyl)-3-(4-tolyl)pyrazole-4-carboxamide

HRID 582010Notes

Reaction equation

[C:1]([C:3](=[C:7](SC)[C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=1)[C:4]([NH2:6])=[O:5])#[N:2].[NH:17]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=1)[NH2:18]>>[NH2:2][C:1]1[N:17]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=2)[N:18]=[C:7]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)[C:3]=1[C:4]([NH2:6])=[O:5]

Participants

Reactant 2

HCID 786452-Hydrazinopyridine

HCID 542422372-Cyano-3-methylthio-3-(4-tolyl)acrylamide2×

Product 1

HCID 545536065-Amino-1-(2-pyridyl)-3-(4-tolyl)pyrazole-4-carboxamide

Procedure

The title compound was prepared from 2-cyano-3-methylthio-3-(4-tolyl)acrylamide (4.64 mg, 2.0 mmol) and 2-hydrazinopyridine (218 mg, 2.0 mmol) following the procedure used for the compound of Example 12. The title compound was obtained as a white crystalline solid (350 mg) m.p. 244-247°. δH (d6DMSO) 8.46 (1H, dm, J 5.0 Hz), 7.97 (1H, ddd, J 8.4, 7.4, 1.9 Hz), 7.85 (1H, d, J 8.4 Hz), 7.68 (2H, br s), 7.47 (2H, d, J 8.1 Hz), 7.31 (2H, d, J 7.6 Hz), 7.29 (1H, signal obscured by overlapping d), 3.30 (2H, s) and 2.37 (3H, s). MS (ES+) 294 (MH+, 100%).

Sources & evidence

ORD record: ord-22ffe1c4effd47a9abd79220ffb84d19
Source dataset: uspto-grants-1999_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05922741

Reaction notes

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