2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-vinyl]-5-(3-methoxy-prop-1-ynyl)-1H-pyrrolo[2,3-b]pyridine → HCID 53251247, 화합물
반응식
[CH:1]1([CH:6]=[C:7]([C:18]2[NH:31][C:21]3=[N:22][CH:23]=[C:24]([C:26]#[C:27][CH2:28][O:29][CH3:30])[CH:25]=[C:20]3[CH:19]=2)[C:8]2[CH:13]=[CH:12][C:11]([S:14]([CH3:17])(=[O:16])=[O:15])=[CH:10][CH:9]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1>[Pd].CO>[CH:1]1([CH2:6][CH:7]([C:18]2[NH:31][C:21]3=[N:22][CH:23]=[C:24]([CH2:26][CH2:27][CH2:28][O:29][CH3:30])[CH:25]=[C:20]3[CH:19]=2)[C:8]2[CH:13]=[CH:12][C:11]([S:14]([CH3:17])(=[O:16])=[O:15])=[CH:10][CH:9]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1참가 물질
4
반응 조건
- 온도
- 50 °C
실험 절차
A mixture of 2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-vinyl]-5-(3-methoxy-prop-1-ynyl)-1H-pyrrolo[2,3-b]pyridine (302 mg, 0.7 mmol) and 10% palladium on activated carbon (80 mg) in methanol (250 mL) was heated at 50° C. under hydrogen (50 psi) for 8 h. The mixture was cooled to room temperature. The catalyst was removed by filtration and washed with ethyl acetate. The filtrate was concentrated in vacuo. Purification using a Waters automated flash system (column: Xterra 30 mm×100 mm, sample manager 2767, pump 2525, detector: ZQ mass and UV 2487, solvent system: acetonitrile and 0.1% ammonium hydroxide in water) afforded 2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-ethyl]-5-(3-methoxy-propyl)-1H-pyrrolo[2,3-b]pyridine (100 mg, 32.5%) as a colorless oil: LC/MS m/e calcd for C25H32N2O3S [M+H]+ 441.61, observed 441.1; 1H NMR (400 MHz, CD3OD) δ ppm 8.25 (s, 1H), 8.10 (br. s., 1H), 7.90-7.95 (m, J=8.1 Hz, 2H), 7.60-7.65 (m, J=8.3 Hz, 2H), 6.65 (s, 1H), 4.39 (t, J=7.8 Hz, 1H), 3.43 (t, J=6.2 Hz, 2H), 3.35 (s, 3H), 3.11 (s, 3H), 2.88 (t, J=7.6 Hz, 2H), 2.26-2.34 (m, 1H), 2.13-2.22 (m, 1H), 1.92-1.99 (m, 2H), 1.63-1.89 (m, 5H), 1.46-1.58 (m, 2H), 1.19-1.34 (m, 2H).