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3-{1-ethoxy-1-phenylmethylidene}-5-nitro-2-indolinone[ No CAS ]
[ 72299-67-3 ]
Yield
Reaction Conditions
Operation in experiment
Prepared from 3-{1-ethoxy-1-phenylmethylidene}-5-nitro-2-indolinone and 1.1 equivalents of an oily mixture of 2-Boc-6-amino-1,2,3,4-tetrahydro-isoquinoline [prepared from <strong>[23687-26-5]6-amino-isoquinoline</strong>, melting point 218-220° C., by catalytic hydrogenation to obtain 6-amino-1,2,3,4-tetrahydro-isoquinoline (melting point: 69-71° C.) and subsequent reaction with 0.9 equivalents of di-tert.butyl pyrocarbonate (=(Boc)2 O)] in DMF by heating to 100° C. for 3.5 hours, pouring into water, filtering and washing the precipitate with water and EtOH.
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane; at 20℃; for 216h;
Intermediate 34: 1 ,1-Dimethylethyl 6-r(1 H-pyrazol-4-ylcarbonyl)aminol-3,4-dihvdro- 2(1 HVisoalphauinolinecarboxylate; To a solution of 1 H-<strong>[37718-11-9]pyrazole-4-carboxylic acid</strong> (800 mg, 7.1 mmol), N-(3- dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride (1.48 g, 7.74 mmol), 1- hydroxybenzotriazole hydrate (1.04 g, 7.74 mmol) and triethylamine (1.8 ml_, 12.9 mmol) in DCM was added 1 , 1 -dimethylethyl 6-amino-3,4-dihydro-2(1 /-/)- isoquinolinecarboxylate (1.6 g, 6.45 mmol) and the reaction mixture was stirred at room temperature for 9 days. The organic phase was washed with 1 N sodium hydroxide, dried over Na2SO4, filtered and evaporated under reduced pressure. The residue was purified by flash column chromatography eluting with DCM/MeOH: 90/10 to give the title compound as a solid (580 mg, 24percent). LC/MS: m/z 341 (M-H)+, Rt: 2.70 min.
Synthesis of 6-(3,5-Dichloro-benzyloxycarbonylamino)-3,4-dihydro-1 H- isoquinoline-2-carboxylic acid tert-butyl ester (46)Starting material 45 (250 mg, 1.4 mmol) and 1 ,1 '-carbonyl diimidazol (275 mg, 1.7 mmol) were dissolved in 2 ml DCM and stirred at room temperature for 3 h. Then starting material 44 (350 mg, 1.4 mmol) was added and the resulting mixture was stirred over night at room temperature. The reaction mixture was diluted with ethyl acetate, the organic phase was washed with water 3 times, dried over Na2SO4, filtered and concentrated in vacuo. The remaining solid was purified over the prep. HPLC (Method 1), pure fractions were combined and concentrated in vacuo yielding the desired product 46 as brown solid (170 mg, 0.377 mmol, 27%).
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