[NH2:1][C:2]1[C:3]([C:18](O)=[O:19])=[N:4][C:5]([CH:8]2[CH2:17][CH2:16][C:11]3([O:15][CH2:14][CH2:13][O:12]3)[CH2:10][CH2:9]2)=[CH:6][CH:7]=1.[CH3:21][N:22](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>>[NH2:1][C:2]1[C:3]([C:18]([NH:22][CH3:21])=[O:19])=[N:4][C:5]([CH:8]2[CH2:9][CH2:10][C:11]3([O:12][CH2:13][CH2:14][O:15]3)[CH2:16][CH2:17]2)=[CH:6][CH:7]=1A solution of 3-amino-6-(1,4-dioxaspiro[4.5]dec-8-yl)pyridine-2-carboxylic acid (Compound 232D, 0.229 g, 0.823 mmol) in DMF (2.0 mL, 26 mmol) was cooled to 0° C. treated with DIPEA (2.87 mL, 16.4 mmol), methylamine hydrochloride (0.556 g, 8.23 mmol) and TBTU (0.396 g, 1.23 mmol). The flask was sealed and the mixture was allowed to come up to RT and stir overnight. The DMF and DIPEA were removed in vacuo and the residue was taken up in water and extracted multiple times with EtOAc and DCM. The combined organic layers were dried over Na2SO4, filtered and concentrated to a yellow oil. This was purified on an ISCO Combiflash unit using 0-4% MeOH/DCM to isolate 145 mg of an oil. 1H NMR (400 MHz, DMSO-d6) δ 1.51-1.87 (m, 8H), 2.54-2.64 (m, 1H), 2.79 (d, J=4.80 Hz, 3H), 3.88 (s, 4H), 6.62 (s, 2H), 7.05-7.10 (m, 1H), 7.11-7.16 (m, 1H), 8.29 (d, J=4.55 Hz, 1H). MS (ES+): m/z=292.01 (100) [M+1]. HPLC: tR=3.31 min (ZQ3, polar—5 min).
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