Hydrazine → 4-(5-amino-6-(hydrazinecarbonyl)pyrazin-2-yl)-N,N-dimethylbenzamide

HRID 78591

Reaction equation

HRID 78591 reaction equation
[NH2:1][C:2]1[C:3]([C:19]([O:21]C)=O)=[N:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14](=[O:18])[N:15]([CH3:17])[CH3:16])=[CH:10][CH:9]=2)=[CH:6][N:7]=1.[NH2:23][NH2:24]>CCO>[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]([C:14]([N:15]([CH3:16])[CH3:17])=[O:18])=[CH:12][CH:13]=2)=[N:4][C:3]=1[C:19]([NH:23][NH2:24])=[O:21]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 59471801Methyl 3-amino-6-(4-(dimethylcarbamoyl)phenyl)pyrazine-2-carboxylate

Product 1

HCID 594716414-(5-amino-6-(hydrazinecarbonyl)pyrazin-2-yl)-N,N-dimethylbenzamideYield 87%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of methyl 3-amino-6-[4-(dimethylcarbamoyl)phenyl]pyrazine-2-carboxylate (1.7011 g, 5.664 mmol) in EtOH (10.21 mL) was added hydrazine (726.1 mg, 711.2 μL, 22.66 mmol). The resultant solution was heated to reflux for 30 minutes and then allowed to cool to RT. The precipitate was filtered off and dried (1.47 g, 87% Yield). 1H NMR (400.0 MHz, DMSO) d 2.96 (s, 3H), 3.00 (s, 3H), 4.58 (d, J=4.4 Hz, 2H), 7.46 (d, J=8.4 Hz, 2H), 8.27-8.29 (m, 2H), 8.88 (s, 1H) and 10.09 (s, 1H) ppm; MS (ES+) 301.13

Workup

  1. temperatureto reflux for 30 minutes
  2. filtrationThe precipitate was filtered off
  3. customdried (1.47 g, 87% Yield)

Sources & evidence

ORD record
ord-4036d8208b69412e87017d520fb06007
Source dataset
uspto-grants-2014_09
Patent number
US08841308B2

Linked notes

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