2-(2-ethoxyphenyl)ethanamine

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:140.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 3-bromo-6-fluoro-imidazo[1,2-b]pyridazine (648 mg, 3 mmol), 2-ethoxy-phenethylamine (1 g, 6 mmol) and triethylamine (1 ml) in isopropyl alcohol (2 ml) was heated in a microwave at 140° C. for 20 min. The reaction mixture was concentrated and the residue was subjected to ISCO (40 g column), to gave the titled compound (980 mg). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.47 (t, J=6.95 Hz, 3H) 3.04 (t, J=6.69 Hz, 2H) 3.64-3.72 (m, 2H) 4.06-4.17 (m, 2H) 4.97 (br. s., 1H) 6.40 (d, J=9.60 Hz, 1H) 6.87-7.02 (m, 2H) 7.17-7.32 (m, 2H) 7.47 (s, 1H) 7.54 (d, J=9.60 Hz, 1H). LRMS (ESI) m/z 361 and 363.1 [(M+H)]+, calc'd for C16H17BrN4O: 361.24. The reaction mixture was concentrated

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

Procedure: Similar procedure as described in example 40c was used, starting from 5-(4-ethoxy-quinolin-6-ylmethylene)-2-methylsulfanyl-thiazol-4-one (example 40b), 2-(2-ethoxy-phenyl)-ethylamine and DIEA to give 2-[2-(2-ethoxy-phenyl)-ethylamino]-5-[1-(4-ethoxy-quinolin-6-yl)-meth-(Z)-ylidene]-thiazol-4-one. LC-MS m/e 448 (MH+).

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

Procedure: Similar procedure as described in example 40c was used, starting from 5-(4-ethoxy-quinolin-6-ylmethylene)-2-methylsulfanyl-thiazol-4-one (example 40b), 2-(2-ethoxy-phenyl)-ethylamine and DIEA to give 2-[2-(2-ethoxy-phenyl)-ethylamino]-5-[1-(4-ethoxy-quinolin-6-yl)-meth-(Z)-ylidene]-thiazol-4-one. LC-MS m/e 448 (MH+).

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-(2-Ethoxyphenyl)ethanamine (0.55 g, 3.33 mmol) and 3-(4-hydroxyphenyl)propanoic acid (0.50 g, 3.00 mmol) was dissolved in dimethyl formamide (5 ml) and cooled to 0° C. N-[(1H-1,2,3-benzotriazol-1-yloxy)(dimethylamino)methylene]-N-methylmethanaminium tetrafluoroborate (1.18 g, 3.66 mmol) and diisopropylethylamine (0.90 g, 7.0 mmol) were added and the solution was warmed to room temperature and stirred overnight. EtOAc (15 ml) was added and the organic phase was washed with two portions of sodium hydrogencarbonate (aq, 10 ml). The organic phase was dried (MgSO4) and EtOAc was removed by evaporation to give 0.98 gram of N-[2-(2-ethoxyphenyl)ethyl]-3-(4-hydroxyphenyl)propanamide (yield 93.9%). the solution was warmed to room temperature the organic phase was washed with two portions of sodium hydrogencarbonate (aq, 10 ml) The organic phase was dried (MgSO4) and EtOAc was removed by evaporation

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

Procedure: Similar procedure as described in example 1b was used, starting from 2-methylsulfanyl-5-[1-quinolin-6-yl-meth-(Z)-ylidene]-thiazol-4-one, 2-(2-Ethoxy-phenyl)-ethylamine and DIEA to give 2-[2-(2-ethoxy-phenyl)-ethylamino]-5-[1-quinolin-6-yl-meth-(Z)-ylidene]-thiazol-4-one. LC-MS m/e 404 (MH+).

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

Procedure: The title compound was prepared from (2S)-3-[4-(1-carboxy-1-methyl-ethoxy)-phenyl]-2-ethoxy-propionic acid ethyl ester (EXAMPLE 49, step 2) and 2-(2-ethoxy-phenyl)-ethylamine via the same procedure used for the preparation of (2S,1R)-2-ethoxy-3-(4-{1-[2-(4-phenoxy-phenyl)-ethylcarbamoyl]-ethoxy}-phenyl)-propionic acid (Example 1, step 3) to produce a colorless oil. MS (ES) for C25H33NO6 [M+H]+: 444. to produce a colorless oil

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

Procedure: The title compound was prepared from (2S)-3-[4-(1-carboxy-1-methyl-ethoxy)-phenyl]-2-methoxy-propionic acid ethyl ester (PREPARATION 5, step 2) and 2-(2-ethoxy-phenyl)-ethylamine via the same procedure used for the preparation of (2S,1R)-2-ethoxy-3-(4-{1-[2-(4-phenoxy-phenyl)-ethylcarbamoyl]-ethoxy}-phenyl)-propionic acid (Example 1, step 3) to produce a colorless oil. MS (ES) for C24H31NO6 [M+H]+: 430. to produce a colorless oil

Conditions: temp:140.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 3-bromo-6-fluoro-imidazo[1,2-b]pyridazine (648 mg, 3 mmol), 2-ethoxy-phenethylamine (1 g, 6 mmol) and triethylamine (1 ml) in isopropyl alcohol (2 ml) was heated in a microwave at 140° C. for 20 min. The reaction mixture was concentrated and the residue was subjected to ISCO (40 g column), to gave the titled compound (980 mg). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.47 (t, J=6.95 Hz, 3H) 3.04 (t, J=6.69 Hz, 2H) 3.64-3.72 (m, 2H) 4.06-4.17 (m, 2H) 4.97 (br. s., 1H) 6.40 (d, J=9.60 Hz, 1H) 6.87-7.02 (m, 2H) 7.17-7.32 (m, 2H) 7.47 (s, 1H) 7.54 (d, J=9.60 Hz, 1H). LRMS (ESI) m/z 361 and 363.1 [(M+H)]+, calc'd for C16H17BrN4O: 361.24. The reaction mixture was concentrated

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

Procedure: Similar procedure as described in example 40c was used, starting from 5-(4-ethoxy-quinolin-6-ylmethylene)-2-methylsulfanyl-thiazol-4-one (example 40b), 2-(2-ethoxy-phenyl)-ethylamine and DIEA to give 2-[2-(2-ethoxy-phenyl)-ethylamino]-5-[1-(4-ethoxy-quinolin-6-yl)-meth-(Z)-ylidene]-thiazol-4-one. LC-MS m/e 448 (MH+).