Cyclopropylamine → HCID 78322289, compound
Reaction equation
[CH:1]1([N:6]2[C:10]3=[N:11][CH:12]=[CH:13][CH:14]=[C:9]3[N:8]=[C:7]2[C:15]([O:17]CC)=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH:20]1([NH2:23])[CH2:22][CH2:21]1>C(O)C>[CH:1]1([N:6]2[C:10]3=[N:11][CH:12]=[CH:13][CH:14]=[C:9]3[N:8]=[C:7]2[C:15]([NH:23][CH:20]2[CH2:22][CH2:21]2)=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of ethyl 3-cyclopentyl-3H-imidazo[4,5-b]pyridine-2-carboxylate (C7) (0.12 g, 0.46 mmol) in ethanol (10 mL) was added cyclopropylamine (0.55 g, 9.6 mmol), and the reaction mixture was stirred at room temperature for 18 hours. After concentration in vacuo, purification was effected via preparative thin layer chromatography on silica gel (Eluent: 5:1 petroleum ether/ethyl acetate) to afford the product as a yellow solid. Yield: 36 mg, 0.13 mmol, 28%. LCMS m/z 270.9 [M+H]+. 1H NMR (400 MHz, CDCl3) δ 8.47 (dd, J=4.6, 1.5 Hz, 1H), 8.02 (br d, J=8 Hz, 1H), 7.85 (br s, 1H), 7.27 (dd, J=8.2, 4.6 Hz, 1H, assumed; partially obscured by solvent peak), 6.16-6.27 (m, 1H), 2.89-2.97 (m, 1H), 2.51-2.64 (m, 2H), 2.06-2.19 (m, 4H), 1.69-1.81 (m, 2H), 0.87-0.95 (m, 2H), 0.69-0.76 (m, 2H).