1-phenoxypropan-2-amine

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

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

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

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

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

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

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

Conditions: temp:25.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a 100 mL round-bottomed flask, HBTU (78 mg, 0.21 mmol), Hunig's base (0.14 ml, 0.79 mmol) and 2-(6-fluoro-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (70 mg, 0.16 mmol) were combined with DMF (3 ml) to give a light yellow solution. 1-Phenoxypropan-2-amine (48 mg, 0.32 mmol) was added and the reaction mixture was stirred at 25° C. for 16 h. The reaction mixture was diluted with EtOAc. The reaction mixture was poured into 50 mL sat NaHCO3 and extracted with EtOAc (2×50 mL). The organic layers were combined and washed with water (2×50 mL) then dried over MgSO4 and concentrated in vacuo to provide 81 mg (89%) of 2-(6-fluoro-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (1-methyl-2-phenoxy-ethyl)-amide as a white solid. MS: (M+H)+=575. to give a light yellow solution The reaction mixture was poured into 50 mL extracted with EtOAc (2×50 mL) washed with water (2×50 mL) then dried over MgSO4 concentrated in vacuo

Conditions: temp:25.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a 100 mL round-bottomed flask, HBTU (78 mg, 0.21 mmol), Hunig's base (0.14 ml, 0.79 mmol) and 2-(6-fluoro-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (70 mg, 0.16 mmol) were combined with DMF (3 ml) to give a light yellow solution. 1-Phenoxypropan-2-amine (48 mg, 0.32 mmol) was added and the reaction mixture was stirred at 25° C. for 16 h. The reaction mixture was diluted with EtOAc. The reaction mixture was poured into 50 mL sat NaHCO3 and extracted with EtOAc (2×50 mL). The organic layers were combined and washed with water (2×50 mL) then dried over MgSO4 and concentrated in vacuo to provide 81 mg (89%) of 2-(6-fluoro-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (1-methyl-2-phenoxy-ethyl)-amide as a white solid. MS: (M+H)+=575. to give a light yellow solution The reaction mixture was poured into 50 mL extracted with EtOAc (2×50 mL) washed with water (2×50 mL) then dried over MgSO4 concentrated in vacuo

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

Procedure: A mixture of 13.81 g. (0.1 moles) of diethyl phosphite, 20 ml. of water and 20 ml. of ethanol is reacted with a mixture of 15.12 g. (0.1 moles) of 1-methyl-2-phenoxyethyl amine and 30 ml. of ethanol as described in Example 1. 21.4 g. of 1-methyl-2-phenoxyethyl-ammoniumethyl phosphonate is obtained. Yield: 81.9%. Melting point: 95°-96° C. A mixture of 13.81 g

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

Procedure: A mixture of 13.81 g. (0.1 moles) of diethyl phosphite, 20 ml. of water and 20 ml. of ethanol is reacted with a mixture of 15.12 g. (0.1 moles) of 1-methyl-2-phenoxyethyl amine and 30 ml. of ethanol as described in Example 1. 21.4 g. of 1-methyl-2-phenoxyethyl-ammoniumethyl phosphonate is obtained. Yield: 81.9%. Melting point: 95°-96° C. A mixture of 13.81 g

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

Procedure: A mixture of 13.81 g. (0.1 moles) of diethyl phosphite, 20 ml. of water and 20 ml. of ethanol is reacted with a mixture of 15.12 g. (0.1 moles) of 1-methyl-2-phenoxyethyl amine and 30 ml. of ethanol as described in Example 1. 21.4 g. of 1-methyl-2-phenoxyethyl-ammoniumethyl phosphonate is obtained. Yield: 81.9%. A mixture of 13.81 g