HCID 86683665, compound → HCID 53261732, compound
Reaction equation
[O:1]=[C:2]1[C:11]2[C:6](=[N:7][C:8]([C:18]3[CH:23]=[CH:22][C:21]([C:24]4([NH:28]C(=O)OC(C)(C)C)[CH2:27][CH2:26][CH2:25]4)=[CH:20][CH:19]=3)=[C:9]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH:10]=2)[CH2:5][O:4][CH2:3]1>C(O)(C(F)(F)F)=O>[NH2:28][C:24]1([C:21]2[CH:20]=[CH:19][C:18]([C:8]3[N:7]=[C:6]4[CH2:5][O:4][CH2:3][C:2](=[O:1])[C:11]4=[CH:10][C:9]=3[C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[CH:23][CH:22]=2)[CH2:25][CH2:26][CH2:27]1Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
tert-Butyl (1-(4-(5-oxo-3-phenyl-6,8-dihydro-5H-pyrano[3,4-b]pyridin-2-yl)phenyl)cyclobutyl)carbamate (12 mg, 0.026 mmol) was dissolved in TFA (1 mL) and stirred for 30 seconds. The solution was immediately concentrated to dryness under reduced pressure. The residue was dissolved in diethyl ether (˜3 mL) and concentrated to dryness under reduced pressure three times. The residue was then slurried in diethyl ether (3 mL) and after settling the supernatant solvent removed by pipette. This was repeated three times. The remaining solvent was removed by freeze drying overnight to give the desired compound as an off-white solid (10 mg, 77% yield). 1H-NMR (500 MHz, MeOD) δ 8.19 (1H, s), 7.41 (2H, d), 7.32 (2H, d), 7.20-7.24 (3H, m), 7.11-7.15 (2H, m), 4.94 (2H, s), 4.37 (2H, s), 2.59-2.68 (2H, m), 2.39-2.49 (2H, m), 2.06-2.16 (1H, m), 1.79-1.95 (1H, m). LCMS (Method D) RT=0.86 min, M+H+=371.00.