spiro[3,4-dihydrochromene-2,1'-cyclobutane]-4-amine

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

Procedure: The title compound was prepared from Intermediate 3 (150 mg, 0.619 mmol) and 4-(2-cyclopentyloxy-3-methoxyphenyl)butanoic acid (205 mg, 0.739 mmol) in presence of EDCI.HCl (193 mg, 1.012 mmol), HOBt (154 mg, 1.012 mmol) and triethylamine (279 μl, 2.043 mmol) in dichloromethane (10 ml) as described in Example 1 to give 149 mg of the product as a white solid; IR (KBr) 3315, 2945, 1642, 1438, 1244, 1040 cm−1; 1H NMR (300 MHz, CDCl3) δ 1.57-1.70 (m, 10H), 1.97-2.04 (m, 4H), 2.14-2.20 (m, 4H), 2.40-2.47 (m, 2H), 2.66-2.72 (m, 2H), 3.80 (s, 3H), 4.79 (br s, 1H), 5.28 (d, J=6.3 Hz, 1H), 5.56 (d, J=8.4 Hz, 1H), 6.66-6.77 (m, 3H), 6.90-7.04 (m, 2H), 7.14-7.20 (m, 1H); ESI-MS (m/z) 484.26 (M)+.

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

Procedure: The title compound was prepared from Intermediate 3 (100 mg, 0.448 mmol) and 1-naphthylacetic acid (99 mg, 0.531 mmol) in presence of EDCI.HCl (128 mg, 0.672 mmol), HOBt (102 mg, 0.672 mmol) and triethylamine (185 μl, 2.022 mmol) in dichloromethane (10 ml) as described in Example 1 to give 100 mg of the product as a white solid; IR (KBr) 3271, 2938, 1636, 1449, 1244, 778 cm−1; 1H NMR (300 MHz, CDCl3) δ 1.62-1.78 (m, 5H), 2.11-2.30 (m, 3H), 4.09 (q, J=16.8 Hz, 2H), 5.23 (q, J=9.3 Hz, 1H), 5.46 (d, J=7.8 Hz, 1H), 6.52 (t, J=7.2 Hz, 1H), 6.60 (d, J=7.2 Hz, 1H), 7.07 (d, J=7.8 Hz, 1H), 7.37-7.42 (m, 2H), 7.48-7.59 (m, 2H), 7.77 (t, J=6.3 Hz, 1H), 7.84 (d, J=7.8 Hz, 1H), 7.99 (d, J=8.1 Hz, 1H); ESI-MS (m/z) 392.59 (M+H)+.

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

Procedure: The title compound was prepared from Intermediate 3 (100 mg, 0.448 mmol) and 1-naphthylacetic acid (99 mg, 0.531 mmol) in presence of EDCI.HCl (128 mg, 0.672 mmol), HOBt (102 mg, 0.672 mmol) and triethylamine (185 μl, 2.022 mmol) in dichloromethane (10 ml) as described in Example 1 to give 100 mg of the product as a white solid; IR (KBr) 3271, 2938, 1636, 1449, 1244, 778 cm−1; 1H NMR (300 MHz, CDCl3) δ 1.62-1.78 (m, 5H), 2.11-2.30 (m, 3H), 4.09 (q, J=16.8 Hz, 2H), 5.23 (q, J=9.3 Hz, 1H), 5.46 (d, J=7.8 Hz, 1H), 6.52 (t, J=7.2 Hz, 1H), 6.60 (d, J=7.2 Hz, 1H), 7.07 (d, J=7.8 Hz, 1H), 7.37-7.42 (m, 2H), 7.48-7.59 (m, 2H), 7.77 (t, J=6.3 Hz, 1H), 7.84 (d, J=7.8 Hz, 1H), 7.99 (d, J=8.1 Hz, 1H); ESI-MS (m/z) 392.59 (M+H)+.

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

Procedure: The title compound was prepared from Intermediate 3 (150 mg, 0.619 mmol) and 4-(2-cyclopentyloxy-3-methoxyphenyl)butanoic acid (205 mg, 0.739 mmol) in presence of EDCI.HCl (193 mg, 1.012 mmol), HOBt (154 mg, 1.012 mmol) and triethylamine (279 μl, 2.043 mmol) in dichloromethane (10 ml) as described in Example 1 to give 149 mg of the product as a white solid; IR (KBr) 3315, 2945, 1642, 1438, 1244, 1040 cm−1; 1H NMR (300 MHz, CDCl3) δ 1.57-1.70 (m, 10H), 1.97-2.04 (m, 4H), 2.14-2.20 (m, 4H), 2.40-2.47 (m, 2H), 2.66-2.72 (m, 2H), 3.80 (s, 3H), 4.79 (br s, 1H), 5.28 (d, J=6.3 Hz, 1H), 5.56 (d, J=8.4 Hz, 1H), 6.66-6.77 (m, 3H), 6.90-7.04 (m, 2H), 7.14-7.20 (m, 1H); ESI-MS (m/z) 484.26 (M)+.

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

Procedure: The title compound was prepared from Intermediate 3 (100 mg, 0.448 mmol) and 1-naphthylacetic acid (99 mg, 0.531 mmol) in presence of EDCI.HCl (128 mg, 0.672 mmol), HOBt (102 mg, 0.672 mmol) and triethylamine (185 μl, 2.022 mmol) in dichloromethane (10 ml) as described in Example 1 to give 100 mg of the product as a white solid; IR (KBr) 3271, 2938, 1636, 1449, 1244, 778 cm−1; 1H NMR (300 MHz, CDCl3) δ 1.62-1.78 (m, 5H), 2.11-2.30 (m, 3H), 4.09 (q, J=16.8 Hz, 2H), 5.23 (q, J=9.3 Hz, 1H), 5.46 (d, J=7.8 Hz, 1H), 6.52 (t, J=7.2 Hz, 1H), 6.60 (d, J=7.2 Hz, 1H), 7.07 (d, J=7.8 Hz, 1H), 7.37-7.42 (m, 2H), 7.48-7.59 (m, 2H), 7.77 (t, J=6.3 Hz, 1H), 7.84 (d, J=7.8 Hz, 1H), 7.99 (d, J=8.1 Hz, 1H); ESI-MS (m/z) 392.59 (M+H)+.