Ethylenediamine → 2-[5-difluoromethoxy-1-(1-methyl-1H-pyrazol-4-ylmethyl)-1H-indazol-3-yl]-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid tert-butylamide

関与物質

反応手順

To a solution of 2-[5-difluoromethoxy-1-(1-methyl-1H-pyrazol-4-ylmethyl)-1H-indazol-3-yl]-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid tert-butylamide (56 mg, 0.09 mmol) in CH2Cl2 (2 mL) was added trifluoroacetic acid (0.5 mL, 6.5 mmol). The reaction mixture was stirred at room temperature for 3 h then concentrated. The residue was dissolved in CH2Cl2 (2 mL) and ethylenediamine (0.2 mL, 2.96 mmol) was added. The reaction mixture was stirred at room temperature for 30 min then quenched with water and extracted with 5% MeOH/CH2Cl2. The organics were dried over MgSO4 and concentrated. The residue was triturated with EtOAc/Et2O and the product was collected via filtration to afford 29 mg (65%) of 2-[5-difluoromethoxy-1-(1-methyl-1H-pyrazol-4-ylmethyl)-1H-indazol-3-yl]-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid tert-butylamide as a light yellow solid. MS: (M+Na)+=517; 1H NMR (DMSO-d6, 300 MHz): δ (ppm) 12.62 (br. s., 1H), 8.97 (s, 1H), 8.26 (s, 1H), 8.06 (d, J=1.9 Hz, 1H), 7.85 (d, J=9.1 Hz, 1H), 7.74 (s, 1H), 7.65 (s, 1H), 7.38 (s, 1H), 7.27 (dd, J=9.1, 1.9 Hz, 1H), 7.06 (7, J=75 Hz, 1H), 5.51 (s, 2H), 3.19 (s, 6H), 1.36 (s, 9H).

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