Sodium cyanoborohydride → HCID 68650796, compound

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To a stirred solution of 3-amino-6-(3-formylphenyl)-N-methylpyrazine-2-carboxamide (50 mg, 0.19 mmol) and 4-propylbenzylamine (35.7 mg, 0.24 mmol) in TBF (5 mL) was added sodium cyanoborohydride (ca. 5 eq.) and the solution was stirred until refluxed for 1 h. The solvent was removed under reduced pressure. The residue was partitioned between ethyl acetate (50 mL) and saturated aqueous solution of Na2CO3 (10 mL). The phases were separated. The organic layer was washed with saturated aqueous sodium chloride then dried (Na2SO4). Filtration and concentration followed by HPLC purification gave (24 mg, 32% yield) of 3-amino-N-methyl-6-[3-({[(4-propylphenyl)methyl]amino}methyl)phenyl]pyrazine-2-carboxamide: 1H NMR (400 MHz; DMSO-d6): 9.7 (br s, 1H); 9.0 (m, 1H); 8.87 (s, 1H); 8.5 (s, 1H); 8.4 (d, 1H); 7.5 (m, 6H); 7.43 (m, 2H); 4.2 (d, 2H); 2.82 (d, 3H); 2.56 (m, 2H); 1.6 (m, 2H); 0.9 (m, 3H); MS (EI) for C23H27N5O: 390 (MH+).

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