[NH2:1][CH2:2][CH2:3][CH2:4][NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9].Cl[C:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][N:22]=2)[N:17]=[CH:16][C:15]=1[N+:24]([O-:26])=[O:25].C(N(CC)CC)C.O>ClCCl>[N+:24]([C:15]1[CH:16]=[N:17][C:18]2[C:23]([C:14]=1[NH:1][CH2:2][CH2:3][CH2:4][NH:5][C:6](=[O:12])[O:7][C:8]([CH3:9])([CH3:11])[CH3:10])=[N:22][CH:21]=[CH:20][CH:19]=2)([O-:26])=[O:25]A solution of tert-butyl 3-aminopropylcarbamate (15.7 g, 90.2 mmol) in dichloromethane (50 mL) was added dropwise over 30 minutes to a solution of 4-chloro-3-nitro[1,5]naphthyridine (18.0 g, 85.9 mmol) and triethylamine (15.6 mL, 112 mmol) in dichloromethane (235 mL) at room temperature. The reaction mixture was stirred for 2.5 hours and then concentrated under reduced pressure to afford an orange solid. Water (300 mL) was added and the mixture was stirred for 1 hour. The solid was isolated by filtration, washed with water (3×50 mL), and dried under vacuum at 70° C. to afford 29.5 g of tert-butyl 3-[(3-nitro[1,5]naphthyridin-4-yl)amino]propylcarbamate as a yellow solid.
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