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A compound and pharmaceutical technology, applied in the field of compounds, can solve problems such as affecting cell degradation of α-synuclein
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Embodiment 1
[2298] N-(1,3-Dimethyl-1H-pyrazol-4-yl)-4-ethoxy-7H-pyrrolo[2,3-d]pyrimidin-2-amine (E1)
[2299]
[2300] N-(1,3-Dimethyl-1H-pyrazol-4-yl)-4-ethoxy-7-toluenesulfonyl-7H-pyrrolo[2,3-d]pyrimidin-2-amine A solution of (which can be prepared according to D3) (100 mg, 0.234 mmol) and sodium hydroxide (0.586 mL, 1.172 mmol) in isopropanol (10 mL) was stirred at 50 °C overnight. The reaction mixture was concentrated in vacuo. The residue was poured into water and extracted with EtOAc (20 mL x 3). The combined organic layers were washed with Na 2 SO 4 Dry, filter and concentrate in vacuo. The crude product was purified by preparative HPLC to afford the title compound E1 (12 mg, 0.042 mmol, 18.12% yield) as a yellow solid.
[2301] LCMS: 273.1[M+H] + . t R = 1.10 min. (LCMS condition 2)
[2302] 1 H NMR (400MHz, chloroform-d): δ8.66-9.05(m, 1H), 7.80(s, 1H), 6.69(d, J=1.5Hz, 1H), 6.41(d, J=1.8Hz, 1H ), 6.24(s, 1H), 4.53(q, J=7.1Hz, 2H), 3.82(s, 3H), 2.27(s, 3H), 1.47(t,...
Embodiment 2 and 3
[2304] 1-(4-((4-ethoxy-7H-pyrrolo[2,3-d]pyrimidin-2-yl)amino)-3-methyl-1H-pyrazol-1-yl)-2- Methylpropan-2-ol (E2)
[2305] 1-(4-((4-ethoxy-7H-pyrrolo[2,3-d]pyrimidin-2-yl)amino)-5-methyl-1H-pyrazol-1-yl)-2- Methylpropan-2-ol (E3)
[2306]
[2307] 2-Chloro-4-ethoxy-7H-pyrrolo[2,3-d]pyrimidine (which can be prepared according to D1) (200 mg, 1.012 mmol), 1-(4-amino-3-methyl-1H -pyrazol-1-yl)-2-methylpropan-2-ol and 1-(4-amino-5-methyl-1H-pyrazol-1-yl)-2-methylpropan-2-ol Mixture (206mg, 1.214mmol), Pd 2 (dba) 3 (46.3mg, 0.051mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis-(diphenylphosphine) (58.6mg, 0.101mmol) and potassium carbonate (420mg, 3.04 mmol) in 2-butanol (2.0 mL) was microwave irradiated at 120° C. for 45 min. The reaction mixture was quenched with water and extracted with EtOAc (20 mL x 3). The combined organic layers were washed with Na 2 SO 4 Dry, filter and concentrate in vacuo. The crude product was purified by silica gel column chromatography (DCM:M...
Embodiment 4
[2313]N-(5-chloro-1-methyl-1H-pyrazol-4-yl)-4-ethoxy-7H-pyrrolo[2,3-d]-pyrimidin-2-amine (E4)
[2314]
[2315] N-(5-chloro-1-methyl-1H-pyrazol-4-yl)-4-ethoxy-7-tosyl-7H-pyrrolo[2,3-d]-pyrimidine-2 - A solution of the amine (which can be prepared according to D4) (50 mg, 0.112 mmol) and sodium hydroxide (1 mL, 2.0 mmol, 2M in water) in methanol (3 mL) was stirred at 50 °C for 2 hours. The mixture was extracted with ethyl acetate. The organic layer was dried and evaporated. The crude product was purified by preparative HPLC to afford the title compound E4 (19 mg, 0.065 mmol, 58.0% yield) as a white solid.
[2316] LCMS: 293[M+H] + . t R = 1.278 minutes. (LCMS condition 2)
[2317] 1 H NMR (400MHz, methanol-d 4 ): δ7.82-8.01 (m, 1H), 6.86 (d, J = 3.5Hz, 1H), 6.32 (d, J = 3.5Hz, 1H), 4.51 (q, J = 7.0Hz, 2H), 3.85 (s, 3H), 1.44 (t, J=7.2Hz, 3H).
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