Pyridine → 3-Propionylamino-pyrazine-2-carboxylic acid amide

HRID 238240

Reaction equation

HRID 238240 reaction equation
[NH2:1][C:2]1[C:3]([C:8]([OH:10])=O)=[N:4][CH:5]=[CH:6][N:7]=1.N1C=C[CH:14]=[CH:13][CH:12]=1.[NH3:17].[OH2:18]>CN(C1C=CN=CC=1)C.C(OC(=O)CC)(=O)CC>[C:12]([NH:1][C:2]1[C:3]([C:8]([NH2:17])=[O:10])=[N:4][CH:5]=[CH:6][N:7]=1)(=[O:18])[CH2:13][CH3:14]

Participants

6

Reactant 3

HCID 1049PyridineHCID 726563-Amino-2-pyrazinecarboxylic acidHCID 12896473Azane;hydrate

Product 1

HCID 599935133-Propionylamino-pyrazine-2-carboxylic acid amideYield 43%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 31263Propionic anhydrideSolvent

Procedure

A mixture of 3-amino-pyrazine-2-carboxylic acid (20.9 g, 0.15 mol), pyridine (29.6 g, 0.375 mol) and DMAP (1.83 g, 15 mmol) in propionic acid anhydride (100 mL) was stirred at room temperature overnight. The reaction mixture was poured into NH3.H2O (500 mL) partially at 0° C. After stirred for 30 min at 0° C., the precipitated solid was filtered, washed with water, dried in air to give 3-propionylamino-pyrazine-2-carboxylic acid amide as a beige solid (12.4 g, 43%), which was used directly in the next step.

Workup

  1. stirringAfter stirred for 30 min at 0° C.
  2. filtrationthe precipitated solid was filtered
  3. washwashed with water
  4. customdried in air

Sources & evidence

ORD record
ord-e462de6e1306463e8024cdb00ecdc717
Source dataset
uspto-grants-2014_02
Patent number
US08642609B2

Linked notes

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