3-Amino-2-pyrazinecarboxylic acid → 3-Amino-pyrazine-2-carboxylic acid methoxy-methylamide
Reaction equation
[NH2:1][C:2]1[C:3]([C:8]([OH:10])=O)=[N:4][CH:5]=[CH:6][N:7]=1.CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.C(N(C(C)C)CC)(C)C.Cl.[CH3:43][O:44][NH:45][CH3:46]>CN(C=O)C>[CH3:43][O:44][N:45]([CH3:46])[C:8]([C:3]1[C:2]([NH2:1])=[N:7][CH:6]=[CH:5][N:4]=1)=[O:10]Participants
7
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 3-aminopyrazine-2-carboxylic acid (1 g, 7.2 mmol) in DMF (15 ml) is added EDC hydrochloride (1.7 g, 8.6 mmol), HOBt (1.16 g, 8.6 mmol), diisopropylethylamine (3.08 ml, 18 mmol) and N-methoxy-N-methylamine hydrochloride (0.84 g, 8.6 mmol), and the resulting solution is stirred at room temperature for 15 hours. The reaction is concentrated in vacuo, and sat. aq. NaHCO3 (50 ml) is added to the residue. The product is extracted into EtOAc (3×60 ml), washed with sat. aq. NaCl (2×50 ml), dried (MgSO4) and concentrated in vacuo to afford a yellow residue. Purification by flash chromatography (SiO2, 0-5% MeOH in DCM) yields 3-amino-pyrazine-2-carboxylic acid methoxy-methylamide as a yellow solid.
Workup
- concentrationThe reaction is concentrated in vacuo, and sat. aq. NaHCO3 (50 ml)
- additionis added to the residue
- extractionThe product is extracted into EtOAc (3×60 ml)
- washwashed with sat. aq. NaCl (2×50 ml)
- dry with materialdried (MgSO4)
- concentrationconcentrated in vacuo
- customto afford a yellow residue
- customPurification by flash chromatography (SiO2, 0-5% MeOH in DCM)
Sources & evidence
- ORD record
- ord-0a69cad95a25465bb9fb417704dcf823
- Source dataset
- uspto-grants-2012_09
- Patent number
- US08268834B2
Reaction notes
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