1-(oxolan-2-yl)-2-phenylethanone

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 2-phenyl-1-(tetrahydrofuran-2-yl)ethanone (Intermediate 90) (522 mg, 2.75 mmol), 3-ethoxy-4-hydroxy-5-nitrobenzaldehyde (695 mg, 3.3 mmol), and urea (495 mg, 8.25 mmol) in anhydrous EtOH (4 mL) was added concentrated HCl solution (0.2 mL), the reaction mixture was refluxed for 14 hours. The reaction mixture was concentrated, and purified by column chromatography and preparative HPLC to give product, contaminated with an impurity (21 mg). This was further purified by preparative TLC and preparative HPLC to give Compound 171 (14 mg). 1H NMR (DMSO-d6 400 MHz): δ 10.170 (s, 1H), 8.318 (s, 1H), 7.629 (d, J=2.4 Hz, 1H), 7.276-7.344 (m, 5H), 7.066-7.163 (m, 2H), 5.384 (s, 1H), 4.245 (d, J=4.0 Hz, 1H), 3.844-4.025 (m, 4H), 1.964-2.220 (m, 4H), 1.227-1.262 (t, J=3.0 Hz, 3H); MS (ESI): m/z 426.1 [M+1]+. the reaction mixture was refluxed for 14 hours The reaction mixture was concentrated purified by column chromatography and preparative HPLC to give product This was further purified by preparative TLC and preparative HPLC

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 2-phenyl-1-(tetrahydrofuran-2-yl)ethanone (Intermediate 90) (522 mg, 2.75 mmol), 3-ethoxy-4-hydroxy-5-nitrobenzaldehyde (695 mg, 3.3 mmol), and urea (495 mg, 8.25 mmol) in anhydrous EtOH (4 mL) was added concentrated HCl solution (0.2 mL), the reaction mixture was refluxed for 14 hours. The reaction mixture was concentrated, and purified by column chromatography and preparative HPLC to give product, contaminated with an impurity (21 mg). This was further purified by preparative TLC and preparative HPLC to give Compound 171 (14 mg). 1H NMR (DMSO-d6 400 MHz): δ 10.170 (s, 1H), 8.318 (s, 1H), 7.629 (d, J=2.4 Hz, 1H), 7.276-7.344 (m, 5H), 7.066-7.163 (m, 2H), 5.384 (s, 1H), 4.245 (d, J=4.0 Hz, 1H), 3.844-4.025 (m, 4H), 1.964-2.220 (m, 4H), 1.227-1.262 (t, J=3.0 Hz, 3H); MS (ESI): m/z 426.1 [M+1]+. the reaction mixture was refluxed for 14 hours The reaction mixture was concentrated purified by column chromatography and preparative HPLC to give product This was further purified by preparative TLC and preparative HPLC

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 2-phenyl-1-(tetrahydrofuran-2-yl)ethanone (Intermediate 90) (522 mg, 2.75 mmol), 3-ethoxy-4-hydroxy-5-nitrobenzaldehyde (695 mg, 3.3 mmol), and urea (495 mg, 8.25 mmol) in anhydrous EtOH (4 mL) was added concentrated HCl solution (0.2 mL), the reaction mixture was refluxed for 14 hours. The reaction mixture was concentrated, and purified by column chromatography and preparative HPLC to give product, contaminated with an impurity (21 mg). This was further purified by preparative TLC and preparative HPLC to give Compound 171 (14 mg). 1H NMR (DMSO-d6 400 MHz): δ 10.170 (s, 1H), 8.318 (s, 1H), 7.629 (d, J=2.4 Hz, 1H), 7.276-7.344 (m, 5H), 7.066-7.163 (m, 2H), 5.384 (s, 1H), 4.245 (d, J=4.0 Hz, 1H), 3.844-4.025 (m, 4H), 1.964-2.220 (m, 4H), 1.227-1.262 (t, J=3.0 Hz, 3H); MS (ESI): m/z 426.1 [M+1]+. the reaction mixture was refluxed for 14 hours The reaction mixture was concentrated purified by column chromatography and preparative HPLC to give product This was further purified by preparative TLC and preparative HPLC

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 2-phenyl-1-(tetrahydrofuran-2-yl)ethanone (Intermediate 90) (522 mg, 2.75 mmol), 3-ethoxy-4-hydroxy-5-nitrobenzaldehyde (695 mg, 3.3 mmol), and urea (495 mg, 8.25 mmol) in anhydrous EtOH (4 mL) was added concentrated HCl solution (0.2 mL), the reaction mixture was refluxed for 14 hours. The reaction mixture was concentrated, and purified by column chromatography and preparative HPLC to give product, contaminated with an impurity (21 mg). This was further purified by preparative TLC and preparative HPLC to give Compound 171 (14 mg). 1H NMR (DMSO-d6 400 MHz): δ 10.170 (s, 1H), 8.318 (s, 1H), 7.629 (d, J=2.4 Hz, 1H), 7.276-7.344 (m, 5H), 7.066-7.163 (m, 2H), 5.384 (s, 1H), 4.245 (d, J=4.0 Hz, 1H), 3.844-4.025 (m, 4H), 1.964-2.220 (m, 4H), 1.227-1.262 (t, J=3.0 Hz, 3H); MS (ESI): m/z 426.1 [M+1]+. the reaction mixture was refluxed for 14 hours The reaction mixture was concentrated purified by column chromatography and preparative HPLC to give product This was further purified by preparative TLC and preparative HPLC

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 2-phenyl-1-(tetrahydrofuran-2-yl)ethanone (Intermediate 90) (522 mg, 2.75 mmol), 3-ethoxy-4-hydroxy-5-nitrobenzaldehyde (695 mg, 3.3 mmol), and urea (495 mg, 8.25 mmol) in anhydrous EtOH (4 mL) was added concentrated HCl solution (0.2 mL), the reaction mixture was refluxed for 14 hours. The reaction mixture was concentrated, and purified by column chromatography and preparative HPLC to give product, contaminated with an impurity (21 mg). This was further purified by preparative TLC and preparative HPLC to give Compound 171 (14 mg). 1H NMR (DMSO-d6 400 MHz): δ 10.170 (s, 1H), 8.318 (s, 1H), 7.629 (d, J=2.4 Hz, 1H), 7.276-7.344 (m, 5H), 7.066-7.163 (m, 2H), 5.384 (s, 1H), 4.245 (d, J=4.0 Hz, 1H), 3.844-4.025 (m, 4H), 1.964-2.220 (m, 4H), 1.227-1.262 (t, J=3.0 Hz, 3H); MS (ESI): m/z 426.1 [M+1]+. the reaction mixture was refluxed for 14 hours The reaction mixture was concentrated purified by column chromatography and preparative HPLC to give product This was further purified by preparative TLC and preparative HPLC

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 2-phenyl-1-(tetrahydrofuran-2-yl)ethanone (Intermediate 90) (522 mg, 2.75 mmol), 3-ethoxy-4-hydroxy-5-nitrobenzaldehyde (695 mg, 3.3 mmol), and urea (495 mg, 8.25 mmol) in anhydrous EtOH (4 mL) was added concentrated HCl solution (0.2 mL), the reaction mixture was refluxed for 14 hours. The reaction mixture was concentrated, and purified by column chromatography and preparative HPLC to give product, contaminated with an impurity (21 mg). This was further purified by preparative TLC and preparative HPLC to give Compound 171 (14 mg). 1H NMR (DMSO-d6 400 MHz): δ 10.170 (s, 1H), 8.318 (s, 1H), 7.629 (d, J=2.4 Hz, 1H), 7.276-7.344 (m, 5H), 7.066-7.163 (m, 2H), 5.384 (s, 1H), 4.245 (d, J=4.0 Hz, 1H), 3.844-4.025 (m, 4H), 1.964-2.220 (m, 4H), 1.227-1.262 (t, J=3.0 Hz, 3H); MS (ESI): m/z 426.1 [M+1]+. the reaction mixture was refluxed for 14 hours The reaction mixture was concentrated purified by column chromatography and preparative HPLC to give product This was further purified by preparative TLC and preparative HPLC

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 2-phenyl-1-(tetrahydrofuran-2-yl)ethanone (Intermediate 90) (522 mg, 2.75 mmol), 3-ethoxy-4-hydroxy-5-nitrobenzaldehyde (695 mg, 3.3 mmol), and urea (495 mg, 8.25 mmol) in anhydrous EtOH (4 mL) was added concentrated HCl solution (0.2 mL), the reaction mixture was refluxed for 14 hours. The reaction mixture was concentrated, and purified by column chromatography and preparative HPLC to give product, contaminated with an impurity (21 mg). This was further purified by preparative TLC and preparative HPLC to give Compound 171 (14 mg). 1H NMR (DMSO-d6 400 MHz): δ 10.170 (s, 1H), 8.318 (s, 1H), 7.629 (d, J=2.4 Hz, 1H), 7.276-7.344 (m, 5H), 7.066-7.163 (m, 2H), 5.384 (s, 1H), 4.245 (d, J=4.0 Hz, 1H), 3.844-4.025 (m, 4H), 1.964-2.220 (m, 4H), 1.227-1.262 (t, J=3.0 Hz, 3H); MS (ESI): m/z 426.1 [M+1]+. the reaction mixture was refluxed for 14 hours The reaction mixture was concentrated purified by column chromatography and preparative HPLC to give product This was further purified by preparative TLC and preparative HPLC

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 2-phenyl-1-(tetrahydrofuran-2-yl)ethanone (Intermediate 90) (522 mg, 2.75 mmol), 3-ethoxy-4-hydroxy-5-nitrobenzaldehyde (695 mg, 3.3 mmol), and urea (495 mg, 8.25 mmol) in anhydrous EtOH (4 mL) was added concentrated HCl solution (0.2 mL), the reaction mixture was refluxed for 14 hours. The reaction mixture was concentrated, and purified by column chromatography and preparative HPLC to give product, contaminated with an impurity (21 mg). This was further purified by preparative TLC and preparative HPLC to give Compound 171 (14 mg). 1H NMR (DMSO-d6 400 MHz): δ 10.170 (s, 1H), 8.318 (s, 1H), 7.629 (d, J=2.4 Hz, 1H), 7.276-7.344 (m, 5H), 7.066-7.163 (m, 2H), 5.384 (s, 1H), 4.245 (d, J=4.0 Hz, 1H), 3.844-4.025 (m, 4H), 1.964-2.220 (m, 4H), 1.227-1.262 (t, J=3.0 Hz, 3H); MS (ESI): m/z 426.1 [M+1]+. the reaction mixture was refluxed for 14 hours The reaction mixture was concentrated purified by column chromatography and preparative HPLC to give product This was further purified by preparative TLC and preparative HPLC