2-Pyrazinecarboxylic acid → HCID 22336266, compound

HRID 1934366Notes

Reaction equation

HRID 1934366 reaction equation
CCN=C=NCCCN(C)C.Cl.[N:13]1[CH:18]=[CH:17][N:16]=[CH:15][C:14]=1[C:19]([OH:21])=O.[NH2:22][C:23]([CH3:27])([CH3:26])[CH2:24][OH:25].C1C=CC2N(O)N=NC=2C=1>C(Cl)Cl.C(OCC)(=O)C>[OH:25][CH2:24][C:23]([NH:22][C:19]([C:14]1[CH:15]=[N:16][CH:17]=[CH:18][N:13]=1)=[O:21])([CH3:27])[CH3:26]

Participants

7

Reactant 4

HCID 10472-Pyrazinecarboxylic acidHCID 118072-Amino-2-methyl-1-propanolHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 22336266HCID 22336266, compoundYield 18%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

WSC HCl (1.94 g, 10 mmol) was added to a mixture of 2-pyrazinecarboxylic acid (0.99 g, 8 mmol), 2-amino-2-methyl-1-propanol (0. 80 g, 9 mmol) and HOBt (1.36 g, 10 mmol) in methylene chloride (30 ml), and stirred at room temperature overnight. The reaction mixture was diluted with ethyl acetate and washed with saturated aqueous NaHCO3 and brine, successively, dried over Na2SO4 and concentrated under a reduced pressure. The residue was suspended in methanol (10 ml), added 2N aqueous NaOH to and stirred for 30 minutes. Methanol was evaporated under a reduced pressure, diluted with saturated aqueous NaHCO3 and extracted with chloroform. The extract was washed with with saturated aqueous NaHCO3 and brine, successively, dried over Na2SO4. After the solvent was evaporated, the obtained crystal was washed with hexane and dried to give the title compound (0.27 g; 18%).

Workup

  1. washwashed with saturated aqueous NaHCO3 and brine
  2. dry with materialsuccessively, dried over Na2SO4
  3. concentrationconcentrated under a reduced pressure
  4. additionadded 2N aqueous NaOH to and
  5. stirringstirred for 30 minutes
  6. customMethanol was evaporated under a reduced pressure
  7. additiondiluted with saturated aqueous NaHCO3
  8. extractionextracted with chloroform
  9. washThe extract was washed with with saturated aqueous NaHCO3 and brine
  10. dry with materialsuccessively, dried over Na2SO4
  11. customAfter the solvent was evaporated
  12. washthe obtained crystal was washed with hexane
  13. customdried

Sources & evidence

ORD record
ord-7a3650dd7e5d44ecae3b29368b3bb29b
Source dataset
uspto-grants-2002_05
Patent number
US06384033B1

Reaction notes

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