[NH2:1][C:2]1[C:3]([C:8]([OH:10])=O)=[N:4][CH:5]=[CH:6][CH:7]=1.[CH3:11][N:12](C=O)C.CCN(C(C)C)C(C)C.Cl.CN.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>O>[NH2:1][C:2]1[C:3]([C:8]([NH:12][CH3:11])=[O:10])=[N:4][CH:5]=[CH:6][CH:7]=1A solution of 3-aminopicolinic acid (0.3 g, 2 mmol) in DMF (2.0 mL, 26 mmol) was cooled to 0° C., treated with DIPEA (7.57 mL, 43.4 mmol), methylamine hydrochloride (1.47 g, 21.7 mmol) and TBTU (0.837 g, 2.61 mmol). The flask was sealed and the mixture was allowed to come up to RT stirring for 3 hours. The reaction mixture was poured into water and extracted with EtOAc three times. The combined organic layers were dried over Na2SO4, filtered and concentrated to an oil which was passed through an ion exchange column (SCX). The MeOH/NH3 washes were combined to isolate 108 mg of a brown oil which crystallized upon standing. 1H NMR (400 MHz, DMSO-d6) δ 2.76 (d, J=4.80 Hz, 3H), 6.81 (br. s., 2H), 7.13 (dd, J=8.30, 1.50 Hz, 1H), 7.22 (dd, J=8.30, 4.30 Hz, 1H), 7.77 (dd, J=4.17, 1.39 Hz, 1H), 8.52 (d, J=3.79 Hz, 1H). MS (ES+): m/z=152.04 [MH+].
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