2-[3-aminopropyl(2-hydroxyethyl)amino]ethanol

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: A mixture of 5.0 g. of 4-chloroquinoline, 7.2 g. of bis(2-hydroxyethyl)aminopropylamine, 3.0 g. of sodium carbonate and 25 ml. of isopropanol is heated in a pressure vessel at 150° C. for 17 hours. The resulting mixture is diluted with chloroform, filtered and purified by filtering over silica gel to obtain an oil of 4-[3-bis(2-hydroxyethyl)aminopropyl]amino-quinoline. A mixture of 5.0 g filtered purified by filtering over silica gel

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

Procedure: A mixture of 5.0 g. of 4-chloroquinoline, 7.2 g. of bis(2-hydroxyethyl)aminopropylamine, 3.0 g. of sodium carbonate and 25 ml. of isopropanol is heated in a pressure vessel at 150° C. for 17 hours. The resulting mixture is diluted with chloroform, filtered and purified by filtering over silica gel to obtain an oil of 4-[3-bis(2-hydroxyethyl)aminopropyl]amino-quinoline. A mixture of 5.0 g filtered purified by filtering over silica gel

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

Procedure: A mixture of 5.05 g. of 2-chloroquinoline, 5.5 g. of bis(2-hydroxyethyl)aminopropylamine and 3.0 g. of sodium carbonate is heated in 20 ml. of refluxing isopropanol for 24 hours. The reaction mixture is then filtered, solvent removed in vacuo and the residue chromatographed over silica gel to obtain an oil of 2-[3-bis(2-hydroxyethyl)aminopropyl]amino-quinoline. A mixture of 5.05 g The reaction mixture is then filtered solvent removed in vacuo the residue chromatographed over silica gel

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

Procedure: A mixture of 5.05 g. of 2-chloroquinoline, 5.5 g. of bis(2-hydroxyethyl)aminopropylamine and 3.0 g. of sodium carbonate is heated in 20 ml. of refluxing isopropanol for 24 hours. The reaction mixture is then filtered, solvent removed in vacuo and the residue chromatographed over silica gel to obtain an oil of 2-[3-bis(2-hydroxyethyl)aminopropyl]amino-quinoline. A mixture of 5.05 g The reaction mixture is then filtered solvent removed in vacuo the residue chromatographed over silica gel

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

Procedure: A mixture of 5.0 g. of 4-chloroquinoline, 7.2 g. of bis(2-hydroxyethyl)aminopropylamine, 3.0 g. of sodium carbonate and 25 ml. of isopropanol is heated in a pressure vessel at 150°C. for 17 hours. The resulting mixture is diluted with chloroform, filtered and purified by filtering over silica gel to obtain an oil of 4-[3-bis(2-hydroxyethyl)aminopropyl]amino-quinoline. A mixture of 5.0 g filtered purified by filtering over silica gel

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

Procedure: A mixture of 5.05 g. of 2-chloroquinoline, 5.5 g. of bis(2-hydroxyethyl)aminopropylamine and 3.0 g. of sodium carbonate is heated in 20 ml. of refluxing isopropanol for 24 hours. The reaction mixture is then filtered, solvent removed in vacuo and the residue chromatographed over silica gel to obtain an oil of 2-[3-bis(2-hydroxyethyl)aminopropyl]amino-quinoline. A mixture of 5.05 g The reaction mixture is then filtered solvent removed in vacuo the residue chromatographed over silica gel

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

Procedure: A mixture of 2.8 g. of 7,10-dichloro-2-methoxypyrido [3,2-b]quinoline, 1.8 g. of 3-[bis(2-hydroxyethyl)amino]propylamine and 6.5 g. of phenol was treated as in Example 5 to obtain the title compound, m.p. 243°-245° C. A mixture of 2.8 g

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

Procedure: 3-(2,6-Difluoro-3,5-dimethoxy-phenyl)-1-ethyl-7-methylsulfinyl-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one was prepared using 0.50 g (1.21 mmol) of 3-(2,6-difluoro-3,5-dimethoxy-phenyl)-1-ethyl-7-methylsulfinyl-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one and 0.59 g (3.64 mmol) of N-(3-amino-propyl)diethanolamine. The crude product was purified using medium-pressure chromatography eluting with a gradient of 9:1 ethyl acetate/methanol to 9:1:0.25 to 9:1:0.5 ethyl acetate/methanol/triethylamine to give 0.43 g (69%) of the title compound: mp 128° C.–129° C. MS (APCI) (m+1)/z 511.2. The crude product was purified eluting with a gradient of 9:1 ethyl acetate/methanol to 9:1:0.25 to 9:1:0.5 ethyl acetate/methanol/triethylamine

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

Procedure: A mixture of 5.0 g. of 4-chloroquinoline, 7.2 g. of bis(2-hydroxyethyl)aminopropylamine, 3.0 g. of sodium carbonate and 25 ml. of isopropanol is heated in a pressure vessel at 150° C. for 17 hours. The resulting mixture is diluted with chloroform, filtered and purified by filtering over silica gel to obtain an oil of 4-[3-bis(2-hydroxyethyl)aminopropyl]amino-quinoline. A mixture of 5.0 g filtered purified by filtering over silica gel

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

Procedure: A mixture of 5.05 g. of 2-chloroquinoline, 5.5 g. of bis(2-hydroxyethyl)aminopropylamine and 3.0 g. of sodium carbonate is heated in 20 ml. of refluxing isopropanol for 24 hours. The reaction mixture is then filtered, solvent removed in vacuo and the residue chromatographed over silica gel to obtain an oil of 2-[3-bis(2-hydroxyethyl)aminopropyl]amino-quinoline. A mixture of 5.05 g The reaction mixture is then filtered solvent removed in vacuo the residue chromatographed over silica gel