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

HRID 2204814

Reaction equation

HRID 2204814 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-e076cb99ece64ecaac1675eddb49a9b1
Source dataset
uspto-grants-2016_06
Patent number
US09365557B2

Linked notes

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