3-(3,4-dimethoxyphenyl)propanoyl chloride

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: The compound was synthesized starting from benzimidazol-5-carbohydrazide (176 mg; 1 mmol), TEA (0.153 ml; 1.1 mmol), 3,4-dimethoxyphenylpropionylchloride (228 mg, 1.1 mmol) and Lawesson's reagent (606 mg; 1.5 mmol) as described in method 1; yield: 0.017 g (4.6%); MS m/z: 367.2 [M+H]+; 1H-NMR (DMSO d6, 400 MHz): δ 3.00 (t, 2H, 3J=7.5 Hz); 3.40 (t, 2H, 3J=7.5 Hz); 3.68 (s, 3H); 3.70 (s, 3H); 6.75-6.77 (m, 1H); 6.81-6.83 (m, 1H); 6.89 (br s, 1H); 7.67-7.69 (m, 1H); 7.73-7.75 (m, 1H); 8.09 (br s, 1H); 8.34 (s, 1H; HPLC (METHOD [A]): rt 10.82 min (100%) The compound was synthesized rt 10.82 min (100%)

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: The compound was synthesized starting from benzimidazol-5-carbohydrazide (176 mg; 1 mmol), TEA (0.153 ml; 1.1 mmol), 3,4-dimethoxyphenylpropionylchloride (228 mg, 1.1 mmol) and Lawesson's reagent (606 mg; 1.5 mmol) as described in method 1; yield: 0.017 g (4.6%); MS m/z: 367.2 [M+H]+; 1H-NMR (DMSO d6, 400 MHz): δ 3.00 (t, 2H, 3J=7.5 Hz); 3.40 (t, 2H, 3J=7.5 Hz); 3.68 (s, 3H); 3.70 (s, 3H); 6.75-6.77 (m, 1H); 6.81-6.83 (m, 1H); 6.89 (br s, 1H); 7.67-7.69 (m, 1H); 7.73-7.75 (m, 1H); 8.09 (br s, 1H); 8.34 (s, 1H; HPLC (METHOD [A]): rt 10.82 min (100%) The compound was synthesized rt 10.82 min (100%)

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: The compound was synthesized starting from benzimidazol-5-carbohydrazide (176 mg, 1 mmol), TEA (0.153 ml; 1.1 mmol), 3,4-dimethoxyphenylpropionylchloride (228 mg, 1.1 mmol) and POCl3 (0.5 ml; 5.5 mmol) as described in method 1; yield: 0.019 mg (5.4%); MS m/z: 351.3 [M+H]+; 1H-NMR (DMSO d6, 400 MHz): δ 3.04 (t, 2H, 3J=7.5 Hz); 3.23 (t, 2H, 3J=7.5 Hz); 3.69 (s, 6H); 6.78 (dd, 1H, 4J=1.7 Hz, 3J=8.3 Hz); 6.84 (d, 1H, 3J=8.3 Hz); 6.90 (d, 1H, 4J=1.7 Hz); 7.76 (d, 1H, 3J=8.3 Hz); 7.83 (dd, 1H, 4J=1.7 Hz, 3J=8.3 Hz); 8.17 (br s, 1H), 8.40 (s, 1H); HPLC (METHOD [A]): rt 10.29 min (94.2%) The compound was synthesized rt 10.29 min (94.2%)

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A procedure similar to that in Example 4 was used. 5-benzyl-4-(4-methoxy-phenyl)-thiazol-2-ylamine prepared in Example 1 and 3-(3,4-dimethoxy-phenyl)-propionyl chloride prepared in the step 1 were used as starting materials, allowed to react at 35-40° C. for 10 hours, followed by post-treatment to obtain a crude product, which was purified by a silica gel column chromatography eluted with petroleum ether and ethyl acetate (4:1) to obtain a product as a white solid in a yield of 65.0%, mp: 142-143└. 1H-NMR (CDCl3, 400 MHz) δ: 2.12 (2H, t, J=7.72 Hz), 2.74 (2H, t, J=7.72 Hz), 3.80 (6H, s, 2×OCH3), 3.83 (3H, s, OCH3), 4.18 (2H, s, CH2), 6.51 (1H, dd, J=8.16, 1.96 Hz, ArH), 6.56 (1H, d, J=1.96 Hz, ArH), 6.69 (1H, d, J=8.16 Hz, ArH), 6.83 (2H, d, J=8.68 Hz, ArH), 7.21˜7.33 (5H, m, ArH), 7.42 (2H, d, J=8.68 Hz, ArH), 11.05 (1H, br, CONH); EI-MS m/e (%): 488.1 (M+, 66), 296.0 (100); HREI-MS Calcd. for C28H28N2O4S: 488.1770. found: 488.1764. Anal. Calcd. for C28H28N2O4S: C, 68.83; H, 5.78; N, 5.73. found: C, 68.69; H, 5.67; N, 6.09. to react at 35-40° C. for 10 hours to obtain a crude product, which was purified by a silica gel column chromatography eluted with petroleum ether and ethyl acetate (4:1)

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: The compound was synthesized starting from benzimidazol-5-carbohydrazide (176 mg; 1 mmol), TEA (0.153 ml; 1.1 mmol), 3,4-dimethoxyphenylpropionylchloride (228 mg, 1.1 mmol) and Lawesson's reagent (606 mg; 1.5 mmol) as described in method 1; yield: 0.017 g (4.6%); MS m/z: 367.2 [M+H]+; 1H-NMR (DMSO d6, 400 MHz): δ 3.00 (t, 2H, 3J=7.5 Hz); 3.40 (t, 2H, 3J=7.5 Hz); 3.68 (s, 3H); 3.70 (s, 3H); 6.75-6.77 (m, 1H); 6.81-6.83 (m, 1H); 6.89 (br s, 1H); 7.67-7.69 (m, 1H); 7.73-7.75 (m, 1H); 8.09 (br s, 1H); 8.34 (s, 1H; HPLC (METHOD [A]): rt 10.82 min (100%) The compound was synthesized rt 10.82 min (100%)

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: The compound was synthesized starting from benzimidazol-5-carbohydrazide (176 mg, 1 mmol), TEA (0.153 ml; 1.1 mmol), 3,4-dimethoxyphenylpropionylchloride (228 mg, 1.1 mmol) and POCl3 (0.5 ml; 5.5 mmol) as described in method 1; yield: 0.019 mg (5.4%); MS m/z: 351.3 [M+H]+; 1H-NMR (DMSO d6, 400 MHz): δ 3.04 (t, 2H, 3J=7.5 Hz); 3.23 (t, 2H, 3J=7.5 Hz); 3.69 (s, 6H); 6.78 (dd, 1H, 4J=1.7 Hz, 3J=8.3 Hz); 6.84 (d, 1H, 3J=8.3 Hz); 6.90 (d, 1H, 4J=1.7 Hz); 7.76 (d, 1H, 3J=8.3 Hz); 7.83 (dd, 1H, 4J=1.7 Hz, 3J=8.3 Hz); 8.17 (br s, 1H), 8.40 (s, 1H); HPLC (METHOD [A]): rt 10.29 min (94.2%) The compound was synthesized rt 10.29 min (94.2%)

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A procedure similar to that in Example 4 was used. 5-benzyl-4-(4-methoxy-phenyl)-thiazol-2-ylamine prepared in Example 1 and 3-(3,4-dimethoxy-phenyl)-propionyl chloride prepared in the step 1 were used as starting materials, allowed to react at 35-40° C. for 10 hours, followed by post-treatment to obtain a crude product, which was purified by a silica gel column chromatography eluted with petroleum ether and ethyl acetate (4:1) to obtain a product as a white solid in a yield of 65.0%, mp: 142-143└. 1H-NMR (CDCl3, 400 MHz) δ: 2.12 (2H, t, J=7.72 Hz), 2.74 (2H, t, J=7.72 Hz), 3.80 (6H, s, 2×OCH3), 3.83 (3H, s, OCH3), 4.18 (2H, s, CH2), 6.51 (1H, dd, J=8.16, 1.96 Hz, ArH), 6.56 (1H, d, J=1.96 Hz, ArH), 6.69 (1H, d, J=8.16 Hz, ArH), 6.83 (2H, d, J=8.68 Hz, ArH), 7.21˜7.33 (5H, m, ArH), 7.42 (2H, d, J=8.68 Hz, ArH), 11.05 (1H, br, CONH); EI-MS m/e (%): 488.1 (M+, 66), 296.0 (100); HREI-MS Calcd. for C28H28N2O4S: 488.1770. found: 488.1764. Anal. Calcd. for C28H28N2O4S: C, 68.83; H, 5.78; N, 5.73. found: C, 68.69; H, 5.67; N, 6.09. to react at 35-40° C. for 10 hours to obtain a crude product, which was purified by a silica gel column chromatography eluted with petroleum ether and ethyl acetate (4:1)