Ethylenediamine → 2-[6-fluoro-1-(2-morpholin-4-yl-ethyl)-1H-indazol-3-yl]-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (1-pyridin-4-yl-ethyl)-amide

関与物質

反応手順

2-[6-Fluoro-1-(2-morpholin-4-yl-ethyl)-1H-indazol-3-yl]-5-(2-trimethylsilanylethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (1-pyridin-4-yl-ethyl)-amide (70 mg, 0.11 mmol) was combined with dichloromethane (1 mL) then trifluoroacetic acid (0.24 ml, 3.26 mmol) was added. After stirring for 2 h, the reaction mixture was concentrated in vacuo. The residue was dissolved in dichloromethane (1 mL) and ethylenediamine (0.22 ml, 3.26 mmol) was added. The reaction mixture was stirred for 20 min then concentrated in vacuo. The residue was diluted with water then extracted with CH2Cl2 (2×20 ml). The combined organic layers were dried with MgSO4, filtered and concentrated in vacuo to afford 26 mg (44%) of 2-[6-fluoro-1-(2-morpholin-4-yl-ethyl)-1H-indazol-3-yl]-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (1-pyridin-4-yl-ethyl)-amide as a yellow solid. MS: (M+H)+=515; 1H NMR (DMSO-d6) δ: 9.13 (s, 1H), 8.44-8.62 (m, 4H), 8.35 (dd, J=8.9, 5.4 Hz, 1H), 7.73 (dd, J=10.0, 2.0 Hz, 1H), 7.45 (d, J=6.0 Hz, 2H), 6.98 (d, J=2.0 Hz, 1H), 5.29 (t, J=7.2 Hz, 1H), 4.62 (t, J=6.4 Hz, 2H), 3.42-3.59 (m, 4H), 3.30 (m, 4H), 2.85 (t, J=6.4 Hz, 2H), 1.65 (d, J=7.0 Hz, 3H).

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