Tris(hydroxymethyl)aminomethane → HCID 66854553, 화합물

참여 물질

반응 단계

Mix an aliquot (1 mL) of a 0.25 M solution of (S)-[1-(6-fluoropyridin-3-yl)-pyrrolidin-3-yl]-amine (0.25 mmol) in toluene, an aliquot (1 mL) of a 1.0 M solution of benzo[b]thiophene-3-carboxaldehyde (1.0 mmol) in toluene and add a single activated 4 Å molecular sieve. Stir the reactants at room temperature in air. After 16 h add PS-Trisamine (1.5 mmol) and another single activated 4 Å molecular sieve. Stir the reactants at room temperature in air. After 24 h filter the reaction solution to remove the PS-Trisamine, and add an aliquot (2 mL) of a 0.25 M solution of sodium borohydride (0.5 mmol) in ethanol. Stir the reactants at room temperature in air. After 48 h add methanol (2 mL) to the reactants and agitate vigorously. Remove the excess reactants by ion-exchange chromatography using a 5 g SCX-2 cartridge (0.5 mmol/g SO3H) by wetting it with one column volume of methanol. Apply the mixture to the cartridge and allow it to percolate through the stationary phase (under gravity) into a vial. Wash the cartridge with one column volume of methanol such that these washings also pass into the vial. Replace with a second vial and elute with 3.5N ammonia in methanol (10 mL). Evaporate the solvents from the ammonia washings on a heating block under a stream of nitrogen to give the title compound. 1H NMR (400 MHz, DMSO-d6) δ 7.90-7.98 (2H, m), 7.57 (1H, s), 7.39-7.42 (1H, m), 7.35-7.39 (2H, m), 7.08-7.13 (1H, m), 6.96 (1H, dd, J=8.93, 3.30 Hz), 4.01 (2H, s), 3.43-3.50 (2H, m), 3.20-3.27 (1H, m), 3.17 (1H, d, J=5.14 Hz), 3.07-3.13 (1H, m), 2.10-2.18 (1H, m), 1.87-1.95 (1H, m), MS (ES): m/z=328 [M+H].

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