2-chloro-N-(ethylcarbamoyl)acetamide

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

Procedure: NEt3 (0.20 mL, 1.44 mmol) and then 1-(2-chloro-acetyl)-3-ethyl-urea (121.8 mg, 0.74 mmol) were added to compound 3 (210.7 mg, 0.59 mmol) dissolved in DMF (4 mL) and the mixture stirred three days at RT. The mixture was concentrated and the residue was treated with MeOH (1 mL) and then water (20 mL). The precipitated solid was filtered off, washed with water and dried to yield compound 4, 186.6 mg. The mixture was concentrated the residue was treated with MeOH (1 mL) The precipitated solid was filtered off washed with water dried

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

Procedure: A mixture of compound (2) (0.4 g, 1.27 mmol), N-(chloroacetyl)-N′-ethylurea (0.3 g, 1.8 mmol) and N-ethyldiisopropylamine (0.33 g, 2.5 mmol) in dry DMF (“dimethylformamide”) (5 mL) was stirred at room temperature overnight. The mixture was diluted with water to give 0.49 g of (3) as a solid.

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

Procedure: A solution of aminopyridine (3) (0.73 g, 4.26 mmol), N-(chloroacetyl)-N′-ethylurea (0.84 g, 5.10 mmol) and 2,6-lutidine (0.59 mL, 5.10 mmol) in 1,3-dimethyl-2-imidazolidinone (7 mL) was warmed under nitrogen at 110° C. for 5 hours. The mixture was diluted with EtOAc and washed with water (6×), then adsorbed onto silica by removal of solvent in vacuo. Silica gel chromatography (EtOAc gradient to MeOH/EtOAc (2:23)) provided the product (0.76 mg, 6%) as a solid, mp 290-294° C. (decomposed). washed with water (6×) adsorbed onto silica by removal of solvent in vacuo

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

Procedure: NEt3 (0.20 mL, 1.44 mmol) and then 1-(2-chloro-acetyl)-3-ethyl-urea (121.8 mg, 0.74 mmol) were added to compound 3 (210.7 mg, 0.59 mmol) dissolved in DMF (4 mL) and the mixture stirred three days at RT. The mixture was concentrated and the residue was treated with MeOH (1 mL) and then water (20 mL). The precipitated solid was filtered off, washed with water and dried to yield compound 4, 186.6 mg. The mixture was concentrated the residue was treated with MeOH (1 mL) The precipitated solid was filtered off washed with water dried

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

Procedure: A mixture of compound (2) (0.4 g, 1.27 mmol), N-(chloroacetyl)-N′-ethylurea (0.3 g, 1.8 mmol) and N-ethyldiisopropylamine (0.33 g, 2.5 mmol) in dry DMF (“dimethylformamide”) (5 mL) was stirred at room temperature overnight. The mixture was diluted with water to give 0.49 g of (3) as a solid.

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

Procedure: A solution of aminopyridine (3) (0.73 g, 4.26 mmol), N-(chloroacetyl)-N′-ethylurea (0.84 g, 5.10 mmol) and 2,6-lutidine (0.59 mL, 5.10 mmol) in 1,3-dimethyl-2-imidazolidinone (7 mL) was warmed under nitrogen at 110° C. for 5 hours. The mixture was diluted with EtOAc and washed with water (6×), then adsorbed onto silica by removal of solvent in vacuo. Silica gel chromatography (EtOAc gradient to MeOH/EtOAc (2:23)) provided the product (0.76 mg, 6%) as a solid, mp 290-294° C. (decomposed). washed with water (6×) adsorbed onto silica by removal of solvent in vacuo

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

Procedure: NEt3 (0.20 mL, 1.44 mmol) and then 1-(2-chloro-acetyl)-3-ethyl-urea (121.8 mg, 0.74 mmol) were added to compound 3 (210.7 mg, 0.59 mmol) dissolved in DMF (4 mL) and the mixture stirred three days at RT. The mixture was concentrated and the residue was treated with MeOH (1 mL) and then water (20 mL). The precipitated solid was filtered off, washed with water and dried to yield compound 4, 186.6 mg. The mixture was concentrated the residue was treated with MeOH (1 mL) The precipitated solid was filtered off washed with water dried

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

Procedure: A mixture of compound (2) (0.4 g, 1.27 mmol), N-(chloroacetyl)-N′-ethylurea (0.3 g, 1.8 mmol) and N-ethyldiisopropylamine (0.33 g, 2.5 mmol) in dry DMF (“dimethylformamide”) (5 mL) was stirred at room temperature overnight. The mixture was diluted with water to give 0.49 g of (3) as a solid.

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

Procedure: A solution of aminopyridine (3) (0.73 g, 4.26 mmol), N-(chloroacetyl)-N′-ethylurea (0.84 g, 5.10 mmol) and 2,6-lutidine (0.59 mL, 5.10 mmol) in 1,3-dimethyl-2-imidazolidinone (7 mL) was warmed under nitrogen at 110° C. for 5 hours. The mixture was diluted with EtOAc and washed with water (6×), then adsorbed onto silica by removal of solvent in vacuo. Silica gel chromatography (EtOAc gradient to MeOH/EtOAc (2:23)) provided the product (0.76 mg, 6%) as a solid, mp 290-294° C. (decomposed). washed with water (6×) adsorbed onto silica by removal of solvent in vacuo