反应 #4088686
相关文献 (1)
openreactiondata ↗doi:10.1039/C8SC04228D
反应条件: temp:0.00; pressure:0.00; stir:
来源 ID: ord-64c33b52dec34973b934ee3a511c6ff7暂无可渲染的结构数据
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12 条反应 · 12 篇文献
反应条件: temp:0.00; pressure:0.00; stir:
来源 ID: ord-64c33b52dec34973b934ee3a511c6ff7反应条件: temp:0.00; pressure:0.00; stir:
来源 ID: ord-7be61c8159db474b8e3ddcb5583b1f9d反应条件: temp:0.00; pressure:0.00; stir:
来源 ID: ord-f494783d63294efb96c72c0cf17569a7反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
实验步骤: As described for example 8b, 6-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-nicotinic acid (200 mg, 0.65 mmol) was converted, using 2-aminoethyl isopropylether instead of methylamine, to the title compound (190 mg, 74%) which was obtained as a white solid. MS: m/e=454.1 [M+OAc]−.
来源 ID: ord-6469f36da6404856a96e84933ab91e5a反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
实验步骤: As described for example 8b, 6-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-nicotinic acid (200 mg, 0.65 mmol) was converted, using 2-aminoethyl isopropylether instead of methylamine, to the title compound (190 mg, 74%) which was obtained as a white solid. MS: m/e=454.1 [M+OAc]−.
来源 ID: ord-47e21ff13f43418fb11f1af6a4a15566反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
实验步骤: This material was prepared from 2-methyl-6-[thieno[3,2-b]pyridin-7-yloxy]benzofuran-3-carbonyl chloride 101 and 2-(isopropoxy)ethylamine in a similar manner as that described for example 108. 1H NMR (CD3CN) δ8.49 (1H, d, J=5.6 Hz), 7.91 (1H, d, J=5.6 Hz), 7.82 (1H, d, J=8.6 Hz), 7.54 (1H, d, J=5.6 Hz), 7.41 (1H, d, J=2.3 Hz), 7.20 (1H, dd, J=8.6, 2.3 Hz), 6.67 (1H, bm), 6.63 (1H, d, J=5.3 Hz), 3.8-3.51 (5H, m), 2.66 (3H, s), 1.15 (6H, d, J=6.1 Hz). Anal. Calcd for C22H22N2O4S: C, 64.37; H, 5.40; N, 6.82; S, 7.81. Found: C, 64.35; H, 5.51; N, 6.76; S, 7.74.
来源 ID: ord-899a557d8b5a4745beee3798aa2d5351反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
实验步骤: This material was prepared from 2-methyl-6-[thieno[3,2-b]pyridin-7-yloxy]benzofuran-3-carbonyl chloride 101 and 2-(isopropoxy)ethylamine in a similar manner as that described for example 108. 1H NMR (CD3CN) δ8.49 (1H, d, J=5.6 Hz), 7.91 (1H, d, J=5.6 Hz), 7.82 (1H, d, J=8.6 Hz), 7.54 (1H, d, J=5.6 Hz), 7.41 (1H, d, J=2.3 Hz), 7.20 (1H, dd, J=8.6, 2.3 Hz), 6.67 (1H, bm), 6.63 (1H, d, J=5.3 Hz), 3.8-3.51 (5H, m), 2.66 (3H, s), 1.15 (6H, d, J=6.1 Hz). Anal. Calcd for C22H22N2O4S: C, 64.37; H, 5.40; N, 6.82; S, 7.81. Found: C, 64.35; H, 5.51; N, 6.76; S, 7.74.
来源 ID: ord-899a557d8b5a4745beee3798aa2d5351反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
实验步骤: The title compound was prepared in a manner similar to Example 74 using 6-(4-(4-cyanophenyl)-5-hydroxy-1H-pyrazol-1-yl)nicotinic acid and 2-isopropoxyethanamine 1H NMR (400 MHz, DMSO-d6) δ 1.10 (d, J=6.06 Hz, 6 H) 3.42 (q, J=5.81 Hz, 2 H) 3.48-3.55 (m, 2 H) 3.55-3.64 (m, 1 H) 7.79 (d, J=8.34 Hz, 2 H) 8.15 (br. s., 2 H) 8.42 (d, J=7.58 Hz, 1H) 8.68 (br. s., 1 H) 8.77 (t, J=5.05 Hz, 1 H) 8.92 (s, 1 H) 13.54 (br. s., 1 H). MS m/z [M+H]+ 392.1.
来源 ID: ord-42d6d2769311427eb5637199da2d1627反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
实验步骤: The title compound was prepared in a manner similar to Example 74 using 6-(4-(4-cyanophenyl)-5-hydroxy-1H-pyrazol-1-yl)nicotinic acid and 2-isopropoxyethanamine 1H NMR (400 MHz, DMSO-d6) δ 1.10 (d, J=6.06 Hz, 6 H) 3.42 (q, J=5.81 Hz, 2 H) 3.48-3.55 (m, 2 H) 3.55-3.64 (m, 1 H) 7.79 (d, J=8.34 Hz, 2 H) 8.15 (br. s., 2 H) 8.42 (d, J=7.58 Hz, 1H) 8.68 (br. s., 1 H) 8.77 (t, J=5.05 Hz, 1 H) 8.92 (s, 1 H) 13.54 (br. s., 1 H). MS m/z [M+H]+ 392.1.
来源 ID: ord-42d6d2769311427eb5637199da2d1627反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
实验步骤: The title compound was prepared in a manner similar to Example 74 using 6-(4-(4-cyanophenyl)-5-hydroxy-1H-pyrazol-1-yl)nicotinic acid and 2-isopropoxyethanamine. 1H NMR (400 MHz, DMSO-d6) δ 1.10 (d, J=6.06 Hz, 6H) 3.42 (q, J=5.81 Hz, 2H) 3.48-3.55 (m, 2H) 3.55-3.64 (m, 1H) 7.79 (d, J=8.34 Hz, 2H) 8.15 (br. s., 2H) 8.42 (d, J=7.58 Hz, 1H) 8.68 (br. s., 1H) 8.77 (t, J=5.05 Hz, 1H) 8.92 (s, 1H) 13.54 (br. s., 1H). MS m/z [M+H]+392.1.
来源 ID: ord-f316fe4637604b00a016d7f692cde54f反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
实验步骤: Place 5-(4-formyl-2-methoxyphenoxy)pyrazine-2-carboxamide (Example 719, Part A) (0.700 g, 2.56 mmol), 2-isopropoxyethylamine (0.278 g, 2.69 mmol) and 3 Å molecular sieves in a vial. Add methanol (12.8 mL), cap and stir overnight. Add NaBH4 (0.0969 g, 2.56 mmol) and stir until the gasses stop evolving. Load the reaction mixture directly onto a 25 g ISCO® pre-load column. Dry the column in a vacuum oven at room temperature. Purify by eluting through a 40 g ISCO® column with 5% to 20% (2.0 M NH3 in methanol) in ethyl acetate over 45 minutes. Concentrate the fraction containing the product, then take it up in EtOAc (100 mL). Wash the organic solution with 1.0 N NaOH (2× 25 mL), dry it over Na2SO4 filter and concentrate to give the title compound (0.512 g, 55.5%): TOF MS ES+ 361.2 (M+H)+, HRMS calcd for C18H25N4O4 361.1876 (M+H)+, found 361.1891, time 0.38 min; HPLC [YMC-Pro pack C-18 (150×4.6 mm, S-5 microm), 0.05% TFA/acetonitrile in 0.05% TFA/water at 1.0 mL/min, 10-20% over 5 min, 20-95% over 18], tR=9.4 min, 100% purity. Dry the column in a vacuum oven at room temperature Purify by eluting through a 40 g ISCO® column with 5% to 20% (2.0 M NH3 in methanol) in ethyl acetate over 45 minutes Concentrate the fraction containing the product Wash the organic solution with 1.0 N NaOH (2× 25 mL) dry it over Na2SO4 filter concentrate
来源 ID: ord-b149e64481244a2a90ccf89d92ac0220反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
实验步骤: Place 5-(4-formyl-2-methoxyphenoxy)pyrazine-2-carboxamide (Example 719, Part A) (0.700 g, 2.56 mmol), 2-isopropoxyethylamine (0.278 g, 2.69 mmol) and 3 Å molecular sieves in a vial. Add methanol (12.8 mL), cap and stir overnight. Add NaBH4 (0.0969 g, 2.56 mmol) and stir until the gasses stop evolving. Load the reaction mixture directly onto a 25 g ISCO® pre-load column. Dry the column in a vacuum oven at room temperature. Purify by eluting through a 40 g ISCO® column with 5% to 20% (2.0 M NH3 in methanol) in ethyl acetate over 45 minutes. Concentrate the fraction containing the product, then take it up in EtOAc (100 mL). Wash the organic solution with 1.0 N NaOH (2× 25 mL), dry it over Na2SO4 filter and concentrate to give the title compound (0.512 g, 55.5%): TOF MS ES+ 361.2 (M+H)+, HRMS calcd for C18H25N4O4 361.1876 (M+H)+, found 361.1891, time 0.38 min; HPLC [YMC-Pro pack C-18 (150×4.6 mm, S-5 microm), 0.05% TFA/acetonitrile in 0.05% TFA/water at 1.0 mL/min, 10-20% over 5 min, 20-95% over 18], tR=9.4 min, 100% purity. Dry the column in a vacuum oven at room temperature Purify by eluting through a 40 g ISCO® column with 5% to 20% (2.0 M NH3 in methanol) in ethyl acetate over 45 minutes Concentrate the fraction containing the product Wash the organic solution with 1.0 N NaOH (2× 25 mL) dry it over Na2SO4 filter concentrate
来源 ID: ord-b149e64481244a2a90ccf89d92ac0220PubChem References
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