反応 #45455

反応方程式

N-(4-{4-amino-7-[(1E)-3-aminoprop-1-enyl]thieno[3,2-c]pyridin-3-yl}-2-methoxyphenyl)-1-methyl-1H-indole-2-carboxamide

ethyl 4-oxo-1-piperidinecarboxylate

sodium hydroxide

sodiumtriacetoxy borohydride

→

ethyl 4-({(2E)-3-[4-amino-3-(3-methoxy-4-{[(1-methyl-1H-indol-2-yl)carbonyl]amino}phenyl)thieno[3,2-c]pyridin-7-yl]prop-2-enyl}amino)piperidine-1-carboxylate

溶媒

dichloroethane

dichloromethane

反応条件

後処理

1. 1
   workup.STIRRINGThe two layers were stirred for 15 minutes
2. 2
   ろ過followed by filtration through an Empore™ cartridge, and removal of the solvent
3. 3
   その他The resulting crude product was purified by trituration of the residue in ethanol
4. 4
   その他collection of the title compound (0.030 g, 45%) as a white powder

実験手順

To a suspension of N-(4-{4-amino-7-[(1E)-3-aminoprop-1-enyl]thieno[3,2-c]pyridin-3-yl}-2-methoxyphenyl)-1-methyl-1H-indole-2-carboxamide (0.050 g, 0.104 mmol) and ethyl 4-oxo-1-piperidinecarboxylate (0.017 g, 0.087 mmol) in dichloroethane (1.5 mL) was added sodiumtriacetoxy borohydride (0.036 g, 0.173 mmol). The resulting solution was allowed to stir at room temperature for 12 hours. Upon completion, the reaction solution was treated with an aqueous solution of 10% sodium hydroxide (3 mL) and dichloromethane (3 mL). The two layers were stirred for 15 minutes, followed by filtration through an Empore™ cartridge, and removal of the solvent. The resulting crude product was purified by trituration of the residue in ethanol and collection of the title compound (0.030 g, 45%) as a white powder. LCMS (Conditions a) Rt 3.57 minutes, 639.4 (MH+); 1H NMR (400 MHz, DMSO-d6) δ 9.51 (s, 1 H), 8.01 (dd, J=8.2 Hz, J=7.8 Hz, 1 H), 7.95 (s, 1 H), 7.71 (d, J=8.2 Hz, 1 H), 7.62 (s, 1 H), 7.59 (d, J=8.2 Hz, 1 H), 7.35 (s, 1 H), 7.32 (d, J=8.5 Hz, 1 H), 7.21(d, J=1.9 Hz, 1 H), 7.15 (t, J=7.8 Hz, 1 H), 7.08 (dd, J=8.2 Hz, 1.9 Hz, 1 H), 6.67 (d, J=16.0 Hz, 1 H), 6.29 (td, J=16.4 Hz, J=5.9 Hz, 1 H), 5.61 (s (br), 1 H), 4.04 (s, 3 H), 4.02 (q, J=7.02 Hz, 2 H), 3.91 (s, 3 H), 3.88 (m, 2 H), 3.42 (d, J=5.5 Hz, 2 H), 2.87 (m, 2 H), 2.67 (m, 1 H), 1.83 (m, 2 H), 1.19 (m, 2 H), 1.18 (t, J=7.02 Hz, 3 H).

出典