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[4-(4-fluoro-benzyl)-2R,5S-dimethyl-piperazin-1-yl]-(6-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-methanone[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine; In N,N-dimethyl-formamide; for 5.0h;
6-Methyl-lH-pyrrolo[2,3-b]pyridine-5-carboxylic acid (0.65 g) and 4-fluorobenzyl- 2S,5R-dimethyl piperazine (0.82 g) were dissolved in dry DMF (10 mL) and TBTU (1.18 g) was added followed by triethylamine(l .54 mL). The mixture was stirred for 5 h, whereupon it was poured into water and the solid thus separated was filtered and dried. The crude was purified by silica gel chromatography using ethyl acetate as a solvent (Yield: 0.87 g, Rf. 0.767min, Condition B, M+H+: 380).
To the methanol (10 mL) and water (10 mL) suspension of 6-methyl-lH-pyrrolo[2,3- b]pyridine-5-carboxylic acid methyl ester (0.85 g) was added sodium hydroxide (0.53 g) . The reaction was heated at 70 0C for 2 h. The reaction mixture was concentrated and the residue obtained was redissolved in water. The aqueous solution was acidified with cone, hydrochloric acid to pH 2. The solid thus separated was filtered, washed with water and dried under high vacuum. It was used as such for the next step without any purification (Yield: 0.65 g, Rf: 0.48 min, Condition B, M+H+: 177).
2-[5-[4-(4-fluoro-benzyl)-2R,5S-dimethyl-piperazine-1-carbonyl]-6-methyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]-N-methyl-2-oxo-acetamide[ No CAS ]
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