Acetonitrile → HCID 68650725, compound

HRID 646749Notes

Reaction equation

HRID 646749 reaction equation
[NH2:1][C:2]1[CH:3]([C:17]([O:19][CH3:20])=[O:18])[N:4](C)[C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14]Cl)[CH:9]=2)=[CH:6][N:7]=1.C(#N)C.[CH2:24]([NH2:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C(N(C(C)C)CC)(C)C>C1COCC1>[NH2:1][C:2]1[C:3]([C:17]([O:19][CH3:20])=[O:18])=[N:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14][NH:31][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH:9]=2)=[CH:6][N:7]=1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 7504BenzylamineHCID 81531DiisopropylethylamineHCID 68650701HCID 68650701, compound

Product 1

HCID 68650725HCID 68650725, compoundYield 13%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 3-amino-6-(3-chloromethylphenyl)-N-methylpyrazine-2-carboxylate (30.6 mg, 0.11 mmol.) was taken into acetonitrile (2 mL) and THF (1 mL) followed by addition of benzylamine (12 uL, 0.11 mmol) then diisopropylethylamine (20 uL, 0.11 mmol) and the mixture was allowed to stir at room temperature over six days. The mixture was then concentrated in vacuo and the residue purified by silica gel flash chromatography initially using ethyl acetate as eluent followed by elution with 10% methanol in dichloromethane. The pure fractions were combined and concentrated then dried in vacuo to give methyl 3-amino-6-(3-{[(phenylmethyl)amino]methyl}phenyl)pyrazine-2-carboxylate (4.9 mg, 13% yield) as a yellow amorphous solid: MS (EI) for C20H21N4O2: 349 (MH+).

Workup

  1. concentrationThe mixture was then concentrated in vacuo
  2. customthe residue purified by silica gel flash chromatography initially using ethyl acetate as eluent
  3. washfollowed by elution with 10% methanol in dichloromethane
  4. concentrationconcentrated
  5. customthen dried in vacuo

Sources & evidence

ORD record
ord-0418ee1b5fef447f8bc6b7959f5edc56
Source dataset
uspto-grants-2010_04
Patent number
US07704995B2

Reaction notes

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