tert-butyl N-(2-amino-1-phenylethyl)carbamate

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

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

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

Procedure: This compound was prepared in an analogous manner as 3-{[3-(1H-Pyrrolo[2,3-b]pyridin-4-ylamino)-thiophene-2-carbonyl]-amino}-pyrrolidine-1-carboxylic acid tert-butyl ester using tert-butyl (2-amino-1-phenylethyl)carbamate instead of 1-BOC-3-aminopyrrolidine. LCMS (ESI) 378 (M+H) 1H NMR (400 MHz, DMSO-d6) δ ppm 12.44 (1H, br. s.) 10.72 (1H, s) 8.67 (2H, d, J=4.10 Hz) 8.59 (1H, t, J=5.64 Hz) 8.05 (1H, d, J=6.78 Hz) 7.89 (1H, d, J=5.27 Hz) 7.40-7.50 (3H, m) 7.30 (1H, d, J=5.27 Hz) 7.26 (2H, d, J=2.68 Hz) 6.90 (1H, br. s.) 6.65 (1H, d, J=6.83 Hz) 4.40-4.55 (1H, m) 3.70-3.80 (1H, m) 3.58-3.68 (1H, m)

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

Procedure: This compound was prepared in an analogous manner as 3-{[3-(1H-Pyrrolo[2,3-b]pyridin-4-ylamino)-thiophene-2-carbonyl]-amino}-pyrrolidine-1-carboxylic acid tert-butyl ester using tert-butyl (2-amino-1-phenylethyl)carbamate instead of 1-BOC-3-aminopyrrolidine. LCMS (ESI) 378 (M+H) 1H NMR (400 MHz, DMSO-d6) δ ppm 12.44 (1H, br. s.) 10.72 (1H, s) 8.67 (2H, d, J=4.10 Hz) 8.59 (1H, t, J=5.64 Hz) 8.05 (1H, d, J=6.78 Hz) 7.89 (1H, d, J=5.27 Hz) 7.40-7.50 (3H, m) 7.30 (1H, d, J=5.27 Hz) 7.26 (2H, d, J=2.68 Hz) 6.90 (1H, br. s.) 6.65 (1H, d, J=6.83 Hz) 4.40-4.55 (1H, m) 3.70-3.80 (1H, m) 3.58-3.68 (1H, m)

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

Procedure: A solution of 2-amino-1-phenyl-ethyl-carbamic acid tert-butylester (47 mg, 0.2 mmol), 1-(3-Bromo-propyl)-4-methoxy-benzene (100 mg, 0.44 mmol), potassium carbonate (82 mg, 0.6 mmol) and sodium iodide (5 mg, 0.03 mmol) in acetonitrile is stirred at 80° C. for one night. The reaction mixture is acidified with acetic acid, concentrated under reduced pressure and the product is purified by preparative HPLC-MS (50° C., gradient: 45-65% MeOH/H2O+0.1% TFA). The solvent is removed under reduced pressure. Mass spectrum (ESI+): m/z=533 [M+H]+. concentrated under reduced pressure the product is purified by preparative HPLC-MS (50° C., gradient: 45-65% MeOH/H2O+0.1% TFA) The solvent is removed under reduced pressure

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

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

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

Procedure: This compound was prepared in an analogous manner as 3-{[3-(1H-Pyrrolo[2,3-b]pyridin-4-ylamino)-thiophene-2-carbonyl]-amino}-pyrrolidine-1-carboxylic acid tert-butyl ester using tert-butyl (2-amino-1-phenylethyl)carbamate instead of 1-BOC-3-aminopyrrolidine. LCMS (ESI) 378 (M+H) 1H NMR (400 MHz, DMSO-d6) δ ppm 12.44 (1H, br. s.) 10.72 (1H, s) 8.67 (2H, d, J=4.10 Hz) 8.59 (1H, t, J=5.64 Hz) 8.05 (1H, d, J=6.78 Hz) 7.89 (1H, d, J=5.27 Hz) 7.40-7.50 (3H, m) 7.30 (1H, d, J=5.27 Hz) 7.26 (2H, d, J=2.68 Hz) 6.90 (1H, br. s.) 6.65 (1H, d, J=6.83 Hz) 4.40-4.55 (1H, m) 3.70-3.80 (1H, m) 3.58-3.68 (1H, m)

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

Procedure: A solution of 2-amino-1-phenyl-ethyl-carbamic acid tert-butylester (47 mg, 0.2 mmol), 1-(3-Bromo-propyl)-4-methoxy-benzene (100 mg, 0.44 mmol), potassium carbonate (82 mg, 0.6 mmol) and sodium iodide (5 mg, 0.03 mmol) in acetonitrile is stirred at 80° C. for one night. The reaction mixture is acidified with acetic acid, concentrated under reduced pressure and the product is purified by preparative HPLC-MS (50° C., gradient: 45-65% MeOH/H2O+0.1% TFA). The solvent is removed under reduced pressure. Mass spectrum (ESI+): m/z=533 [M+H]+. concentrated under reduced pressure the product is purified by preparative HPLC-MS (50° C., gradient: 45-65% MeOH/H2O+0.1% TFA) The solvent is removed under reduced pressure

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