N-[4-(氨基甲基)苯基]-2,2-二甲基丙酰胺

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Use a method similar to the General Procedure 1-3 to couple 7-chloro-3-(2,2,2-trifluoroacetyl)-6-trifluoromethanesulfonyloxy-2,3,4,5-tetrahydro-1H-benzo[d]azepine (0.33 g, 0.78 mmol) with a solution of 4-(2,2-dimethyl-propionylamino)-benzylamine (0.32 g, 1.6 mmol) in anhydrous toluene/dioxane (4:1, 10 mL). Purify the crude mixture by chromatography on silica gel eluting with hexane/EtOAc (1:0 to 7:3 gradient over 30 min; 35 mL/min) and then by SCX chromatography to obtain 7-chloro-6-[4-(2,2-dimethyl-propionylamino)-benzylamino]-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine as a yellow oil (0.266 g, 70%). MS (ES+) m/z: 482 (M+H)+. Purify the crude mixture by chromatography on silica gel eluting with hexane/EtOAc (1:0 to 7:3 gradient over 30 min; 35 mL/min)

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Add 4M hydrogen chloride in dioxane (20 mL) to a solution of N-(tert-butoxycarbonyl)-4-(2,2-dimethyl-propionylamino)-benzylamine (2 g, 6.53 mmol) in anhydrous 1,4-dioxane (50 mL) at room temperature. Stir overnight and partition the reaction mixture between saturated aqueous NaHCO3 (200 mL) and DCM (500 mL). Extract the aqueous phase with DCM/iso-propanol (85:15, 2×100 mL) and then with DCM/iso-propanol (3:1, 2×100 mL). Dry the combined organic extracts over Na2SO4, filter and concentrate in vacuo. Purify by SCX chromatography eluting with DCM and DCM/2M ammonia in methanol (1:1) to obtain the title compound as a waxy colorless oil (1.13 g, 84%). MS (ES−) m/z: 205.1 (M−H)−. partition the reaction mixture between saturated aqueous NaHCO3 (200 mL) and DCM (500 mL) Extract the aqueous phase with DCM/iso-propanol (85:15, 2×100 mL) Dry the combined organic extracts over Na2SO4 filter concentrate in vacuo Purify by SCX chromatography eluting with DCM and DCM/2M ammonia in methanol (1:1)