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Redisep 40 g column

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The Redisep 40 g column is a piece of lab equipment designed for chromatographic separation. It is a column with a 40 gram capacity for purification of various compounds.

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7 protocols using redisep 40 g column

1

Synthesis of Furan-3-Carboxaldehyde Imine

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General procedure XI was followed using furan-3-carbaldehyde (19d) (1.80 mL, 20.8 mmol), butylamine (0.25 mL, 2.5 mmol), acetic acid (0.24 mL, 4.2 mmol), and 4 Å molecular sieves (200 mg) in nitromethane (21 mL). The crude product was purified via flash column chromatography (ISCO, Redisep 40 g column, 0–100% EtOAc/hexanes gradient) to afford the title compound as a yellow solid (2.9 g, quant.). Rf (1:1 EtOAc/Hex): 0.83; 1H NMR (400 MHz, CDCl3) δ 7.93 (d, J = 13.5 Hz, 1H), 7.86–7.81 (m, 1H), 7.56–7.48 (m, 1H), 7.39 (d, J = 13.5 Hz, 1H), 6.59–6.55 (m, 1H). 13C NMR (101 MHz, CDCl3) δ 147.3, 145.3, 136.7, 129.6, 118.2, 107.2. No ionization observed by HRMS.
Epplin M.P., Mohan A., Harris L.D., Zhu Z., Strong K.L., Bacsa J., Le P., Menaldino D.S., Traynelis S.F, & Liotta D.C. (2020). Discovery of Dihydropyrrolo[1,2-a]pyrazin-3(4H)-one-Based Second-Generation GluN2C- and GluN2D-Selective Positive Allosteric Modulators (PAMs) of the N-Methyl-d-Aspartate (NMDA) Receptor. Journal of medicinal chemistry, 63(14), 7569-7600.
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2

Synthesis of 1-Methyl-1H-pyrazole-5-carbaldehyde Imine

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General procedure XI was followed using 1-methyl-1H-pyrazole-5-carbaldehyde (19e) (2.00 g, 18.2 mmol), butylamine (0.22 mL, 2.2 mmol), acetic acid (0.21 mL, 3.6 mmol), and 4 Å molecular sieves (200 mg) in nitromethane (18 mL). The crude product was purified via flash column chromatography (ISCO, Redisep 40 g column, 0–100% EtOAc/hexanes gradient) to afford the title compound as a yellow solid (1.7 g, 62%). Rf (1:1 EtOAc/Hex): 0.65; 1H NMR (400 MHz, CDCl3) δ 7.94 (d, J = 13.4 Hz, 1H), 7.54 (d, J = 2.2 Hz, 1H), 7.51 (d, J = 13.4 Hz, 1H), 6.66 (d, J = 2.2 Hz, 1H), 4.02 (s, 3H). 13C NMR (101 MHz, CDCl3) δ 139.4, 137.6, 133.2, 124.4, 107.5, 37.3. HRMS calcd for C6H8O2N3, 154.06110 [M + H]+; found 154.06109 [M +H]+.
Epplin M.P., Mohan A., Harris L.D., Zhu Z., Strong K.L., Bacsa J., Le P., Menaldino D.S., Traynelis S.F, & Liotta D.C. (2020). Discovery of Dihydropyrrolo[1,2-a]pyrazin-3(4H)-one-Based Second-Generation GluN2C- and GluN2D-Selective Positive Allosteric Modulators (PAMs) of the N-Methyl-d-Aspartate (NMDA) Receptor. Journal of medicinal chemistry, 63(14), 7569-7600.
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3

Synthesis of 2-Chloroacetyl-3-Methoxyphenylacetate

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General procedure I was followed using methyl 2-(3-methoxyphenyl)-acetate (8c) (2.23 mL, 13.9 mmol), 1 M tin(IV) chloride in DCM (69.4 mL, 69.4 mmol), and 2-chloroacetyl chloride (4.45 mL, 55.5 mmol) in DCE (14 mL). The crude product was purified via flash column chromatography (ISCO, Redisep 40 g column, 0–50% EtOAc/hexanes gradient) to afford the title compound as a white solid (1.65 g, 46%). Rf (1:1 EtOAC/Hex): 0.66; 1H NMR (399 MHz, CDCl3) δ 7.75 (d, J = 8.7 Hz, 1H), 6.86 (dd, J = 8.7, 2.6 Hz, 1H), 6.78 (d, J = 2.6 Hz, 1H), 4.63 (s, 2H), 3.92 (s, 2H), 3.85 (s, 3H), 3.69 (s, 3H). 13C NMR (100 MHz, CDCl3) δ 191.8, 171.5, 162.8, 138.6, 132.1, 126.6, 119.1, 112.0, 55.5, 51.9, 47.1, 40.6. HRMS calcd for C12H14O4Cl, 257.05751 [M + H]+; found 257.05751 [M + H]+.
Epplin M.P., Mohan A., Harris L.D., Zhu Z., Strong K.L., Bacsa J., Le P., Menaldino D.S., Traynelis S.F, & Liotta D.C. (2020). Discovery of Dihydropyrrolo[1,2-a]pyrazin-3(4H)-one-Based Second-Generation GluN2C- and GluN2D-Selective Positive Allosteric Modulators (PAMs) of the N-Methyl-d-Aspartate (NMDA) Receptor. Journal of medicinal chemistry, 63(14), 7569-7600.
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4

Synthesis of Thiophene-3-Carbaldehyde Derivatives

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General procedure XI was followed using thiophene-3-carbaldehyde (19a) (3.00 g, 26.7 mmol), butylamine (0.32 mL, 3.2 mmol), acetic acid (0.31 mL, 5.4 mmol), and 4 Å molecular sieves (300 mg) in nitromethane (27 mL). The crude product was purified via flash column chromatography (ISCO, Redisep 40 g column, 0–100% EtOAc/hexanes gradient) to afford the title compound as a yellow solid (3.3 g, 79%). Rf (1:1 EtOAc/Hex): 0.58; 1H NMR (500 MHz, CDCl3) δ 8.01 (dd, J = 13.5, 0.5 Hz, 1H), 7.73 (ddd, J = 2.5, 1.3, 0.6 Hz, 1H), 7.49 (d, J = 13.5 Hz, 1H), 7.44 (ddd, J = 5.1, 2.9, 0.7 Hz, 1H), 7.28 (ddd, J = 5.1, 1.3, 0.5 Hz, 3H). 13C NMR (126 MHz, CDCl3) δ 136.7, 132.6, 132.5, 132.2, 128.2, 125.1. HRMS calcd for C6H6O2NS, 156.01138 [M + H]+; found 156.01151 [M + H]+.
Epplin M.P., Mohan A., Harris L.D., Zhu Z., Strong K.L., Bacsa J., Le P., Menaldino D.S., Traynelis S.F, & Liotta D.C. (2020). Discovery of Dihydropyrrolo[1,2-a]pyrazin-3(4H)-one-Based Second-Generation GluN2C- and GluN2D-Selective Positive Allosteric Modulators (PAMs) of the N-Methyl-d-Aspartate (NMDA) Receptor. Journal of medicinal chemistry, 63(14), 7569-7600.
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5

Synthesis of 2-(Thiophen-2-yl)Acetamide

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General procedure V was followed using 2-(thiophen-2-yl)ethan-1-amine (21f) (2.00 g, 15.7 mmol), triethylamine (3.18 mL, 31.4 mmol), and 2-chloroacetyl chloride (1.51 mL, 18.9 mmol) in DCM (57 mL). The crude product was purified via flash column chromatography (ISCO, Redisep 40 g column, 0–60% EtOAc/hexanes gradient) to afford the title compound as a red oil (2.64 g, 82%). Rf (1:1 EtOAc/Hex): 0.51; 1H NMR (500 MHz, CDCl3) δ 7.18 (dd, J = 5.2, 1.2 Hz, 1H), 6.95 (dd, J = 5.1, 3.4 Hz, 1H), 6.88–6.83 (m, 1H), 6.75 (s, 1H), 4.03 (s, 2H), 3.58 (q, J = 6.7 Hz, 2H), 3.07 (t, J = 6.7 Hz, 2H). 13C NMR (126 MHz, CDCl3) δ 165.9, 140.6, 127.2, 125.6, 124.2, 42.7, 41.1, 29.7. HRMS calcd for C8H10ONClNaS, 226.00638 [M + Na]+; found 226.00658 [M + Na]+.
Epplin M.P., Mohan A., Harris L.D., Zhu Z., Strong K.L., Bacsa J., Le P., Menaldino D.S., Traynelis S.F, & Liotta D.C. (2020). Discovery of Dihydropyrrolo[1,2-a]pyrazin-3(4H)-one-Based Second-Generation GluN2C- and GluN2D-Selective Positive Allosteric Modulators (PAMs) of the N-Methyl-d-Aspartate (NMDA) Receptor. Journal of medicinal chemistry, 63(14), 7569-7600.
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6

Synthesis of N-Chloroacetyl-3,4-Dimethoxyphenethylamine

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General procedure V was followed using compound 3,4-dimethoxyphenethylamine (13) (5.59 mL, 33.1 mmol), triethylamine (9.23 mL, 66.2 mmol), and 2-chloroacetyl chloride (3.16 mL, 39.7 mmol) in dry DCM (120 mL). The crude product was purified via flash column chromatography (ISCO, Redisep 40 g column, 10–80% EtOAc/hexanes gradient) to afford the title compound as a white solid (6.32 g, 74%). Rf (1:1 EtOAc/Hex): 0.56; 1H NMR (300 MHz, CDCl3) δ 6.82 (d, J = 8.0 Hz, 1H), 6.77–6.69 (m, 2H), 6.64 (s, 0H), 4.02 (s, 2H), 3.87 (s, 3H), 3.86 (s, 3H), 3.53 (q, J = 6.9 Hz, 2H), 2.78 (t, J = 7.0 Hz, 2H). 13C NMR (75 MHz, CDCl3) δ 165.7, 149.0, 147.8, 130.8, 120.6, 111.8, 111.3, 55.9, 42.7, 41.1, 35.1. HRMS calcd for C12H17O3NCl, 258.08915 [M + H]+; found 258.08876 [M + H]+.
Epplin M.P., Mohan A., Harris L.D., Zhu Z., Strong K.L., Bacsa J., Le P., Menaldino D.S., Traynelis S.F, & Liotta D.C. (2020). Discovery of Dihydropyrrolo[1,2-a]pyrazin-3(4H)-one-Based Second-Generation GluN2C- and GluN2D-Selective Positive Allosteric Modulators (PAMs) of the N-Methyl-d-Aspartate (NMDA) Receptor. Journal of medicinal chemistry, 63(14), 7569-7600.
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7

Synthesis of 2-Phenylethyl 3,4-Dimethoxybenzyl Ether

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General procedure VIII was followed using compound 15a (2.67 g, 8.11 mmol), phosphorous oxychloride (2.27 mL, 24.3 mmol), and sodium borohydride (0.64 g, 24 mmol) in acetonitrile (~40 mL) and MeOH (~10 mL). The crude product was purified via flash column chromatography (ISCO, Redisep 40 g column, 10–90% EtOAc/hexanes gradient) to afford the title compound as a white foam (1.6 g, 62% over two steps). Rf (1:1 EtOAC/Hex): 0.29; 1H NMR (300 MHz, CDCl3) δ 7.38–7.26 (m, 5H), 6.58 (s, 2H), 4.68–4.50 (m, 2H), 4.17 (dd, J = 8.2, 3.9 Hz, 1H), 3.83 (s, 3H), 3.79 (s, 3H), 3.75–3.62 (m, 2H), 3.25–3.10 (m, 1H), 3.04–2.90 (m, 1H), 2.74 (t, J = 5.8 Hz, 2H). 13C NMR (101 MHz, CDCl3) δ 147.6, 147.1, 138.0, 128.4, 127.8, 127.7, 127.7, 126.6, 111.8, 109.2, 73.3, 72.9, 55.9, 55.8, 55.0, 40.0, 29.0. HRMS calcd for C19H24O3N, 314.17507 [M + H]+; found 314.17453 [M + H]+.
Epplin M.P., Mohan A., Harris L.D., Zhu Z., Strong K.L., Bacsa J., Le P., Menaldino D.S., Traynelis S.F, & Liotta D.C. (2020). Discovery of Dihydropyrrolo[1,2-a]pyrazin-3(4H)-one-Based Second-Generation GluN2C- and GluN2D-Selective Positive Allosteric Modulators (PAMs) of the N-Methyl-d-Aspartate (NMDA) Receptor. Journal of medicinal chemistry, 63(14), 7569-7600.
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