[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:8]=[C:9]3[C:14](=[N:15][CH:16]=2)[NH:13][CH2:12][CH2:11][CH2:10]3)[CH:2]=1.[CH3:17][N:18]=[C:19]=[O:20].CCN(CC)CC.O>C1COCC1>[CH3:17][NH:18][C:19]([N:13]1[C:14]2[C:9](=[CH:8][C:7]([C:3]3[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=3)=[CH:16][N:15]=2)[CH2:10][CH2:11][CH2:12]1)=[O:20]A solution of 6-pyridin-3-yl-1,2,3,4-tetrahydro-[1,8]naphthyridine (40 mg, 0.19 mmol) in 2 mL of THF is added to methyl isocyanate (16 mg, 0.28 mmol) followed by the addition of Et3N (61 mg, 0.60 mmol). The mixture is stirred at ambient temperature for 16 hrs. To the mixture is added 0.5 mL of water, stirred for 5 minutes and concentrated in vacuo. The residue is dissolved in 1 mL of DMF, filtered and purified by reverse phase HPLC to give 23 mg of the titled product.
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