1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 3-Amino-N-methylpyrazine-2-carboxamide

HRID 1887705Notes

Reaction equation

HRID 1887705 reaction equation
[NH2:1][C:2]1[C:3]([C:8]([OH:10])=O)=[N:4][CH:5]=[CH:6][N:7]=1.Cl.CN.C[CH2:15][N:16]=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>CN(C=O)C.C(OCC)(=O)C>[NH2:1][C:2]1[C:3]([C:8]([NH:16][CH3:15])=[O:10])=[N:4][CH:5]=[CH:6][N:7]=1

Participants

8

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 726563-Amino-2-pyrazinecarboxylic acidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 6364545Methylamine hydrochloride

Product 1

HCID 108207483-Amino-N-methylpyrazine-2-carboxamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3-aminopyrazine-2-carboxylic acid (965 mg, 6.94 mmol), methylamine hydrochloride (697 mg, 10.3 mmol), EDCI (1.61 g, 8.4 mmol), HOBt (1.136 g, 8.4 mmol) and DIEA (2.42 mL, 13.9 mmol) in DMF (24 mL) was stirred at room temperature for 48 h. It was diluted with ethyl acetate and washed with saturated sodium bicarbonate, brine and dried over magnesium sulfate. The solvent was removed and the residue was purified by silica gel chromatography (combiflash-companion; DCM/MeOH gradient) to give the title compound.

Workup

  1. washwashed with saturated sodium bicarbonate, brine
  2. dry with materialdried over magnesium sulfate
  3. customThe solvent was removed
  4. customthe residue was purified by silica gel chromatography (combiflash-companion; DCM/MeOH gradient)

Sources & evidence

ORD record
ord-62bd56c7653e455a8870271bfe5ff7c9
Source dataset
uspto-grants-2013_08
Patent number
US08501763B2

Reaction notes

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