2-Pyrazinecarboxylic acid → HCID 68732840, compound

HRID 1175116Notes

Reaction equation

HRID 1175116 reaction equation
[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[C:7]([OH:9])=O.FC(F)(F)C(O)=O.[NH2:17][C:18]([CH3:24])([CH3:23])[C:19]([O:21][CH3:22])=[O:20].C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C>C1COCC1>[CH3:23][C:18]([NH:17][C:7]([C:2]1[CH:3]=[N:4][CH:5]=[CH:6][N:1]=1)=[O:9])([CH3:24])[C:19]([O:21][CH3:22])=[O:20]

Participants

7

Reactant 5

HCID 10472-Pyrazinecarboxylic acidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 86629359HCID 86629359, compound

Product 1

HCID 68732840HCID 68732840, compoundYield 100.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
22 °C

Procedure

To a solution of pyrazine-2-carboxylic acid (0.202 g, 1.6 mmol) in THF (6 mL) at 0° C. were added methyl 2-amino-2-methylpropanoate trifluoroacetate (0.25 g, 1.6 mmol), HOBt (0.22 g, 1.6 mmol), DIEA (0.21 g, 1.6 mmol) and EDCI (0.343 g, 1.8 mmol). The reaction mixture was allowed to stir at 22° C. After 12 h, the reaction mixture was quenched with a saturated solution of sodium bicarbonate and the product partitioned into DCM. The organic layer was dried over MgSO4, filtered and concentrated to give the title compound (0.36 g, 99%). LC/MS: Rt=1.24 min, ES+224 (Formic Acid method).

Workup

  1. customthe reaction mixture was quenched with a saturated solution of sodium bicarbonate
  2. customthe product partitioned into DCM
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c35150fceea24e33aad67c9ca0d56e55
Source dataset
uspto-grants-2010_11
Patent number
US07838673B2

Reaction notes

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