N-(2-(Diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H

To a three-necked flask equipped with a thermometer, 5-formyl-2, 4-dimethyl-1H-pyrrole-3-carboxylic acid (3, 5.50 g, 32.7 mmol) and anhydrous DMF (13.1 mL) were added while being cooled down to 0 °C with an ice-salt bath. To the above mixture was added dropwise a solution of dicyclohexylcarbodiimide (DCC, 10.13 g, 49.0 mmol) in dichloromethane (78.4 mL) under stirring while keeping the reaction temperature between 0 and 2 °C, to which were then added at r.t. 4-dimethylaminopyridine (DMAP, 1.65 g) and N5-Formyl-2, 4-dimethyl-1H-pyrrole-3-carboxylic acid (1204 g) and 6020 mL of dimethylformamide were stirred at room temperature while 1-(3-dimethyl-aminopropyl-3-ethylcarbodiimide hydrochloride (2071 g), hydroxybenzotriazole (1460 g), triethylamine (2016 mL) and diethylethylenediamine (1215 mL) were added. 5-Formyl-2, 4-dimethyl-1H-pyrrole-3-carboxylic acid (1204 g) and 6020 mL of dimethylformamide were stirred at room temperature while 1-(3-dimethyl-aminopropyl-3-ethylcarbodiimide hydrochloride (2071 g), hydroxybenzotriazole (1460 g), triethylamine (2016 mL) and diethylethylenediamine (1215 mL) were added. 5-Formyl-2, 4-dimethyl-1H-pyrrole-3-carboxylic acid (1204 g) and 6020 mL of dimethylformamide were stirred at room temperature while 1-(3-dimethyl-aminopropyl-3-ethylcarbodiimide hydrochloride (2071 g), hydroxybenzotriazole (1460 g), triethylamine (2016 mL) and diethylethylenediamine (1215 mL) were added. 5-Formyl-2, 4-dimethyl-1H-pyrrole-3-carboxylic acid (1204 g) and 6020 mL of dimethylformamide were stirred at room temperature while 1-(3-dimethyl-aminopropyl-3-ethylcarbodiimide hydrochloride (2071 g), hydroxybenzotriazole (1460 g), triethylamine (2016 mL) and diethylethylenediamine (1215 mL) were added. 5-Formyl-2, 4-dimethyl-1H-pyrrole-3-carboxylic acid (1204 g) and 6020 mL of dimethylformamide were stirred at room temperature while 1-(3-dimethyl-aminopropyl-3-ethylcarbodiimide hydrochloride (2071 g), hydroxybenzotriazole (1460 g), triethylamine (2016 mL) and diethylethylenediamine (1215 mL) were added. 5-Formyl-2, 4-dimethyl-1H-pyrrole-3-carboxylic acid (1204 g) and 6020 mL of dimethylformamide were stirred at room temperature while 1-(3-dimethyl-aminopropyl-3-ethylcarbodiimide hydrochloride (2071 g), hydroxybenzotriazole (1460 g), triethylamine (2016 mL) and diethylethylenediamine (1215 mL) were added. General procedure: The substituted acid (5a or 6a, 1.0 mmol), EDC (229 mg, 1.2 mmol) and HOBt (160 mg, 1.2 mmol) were dissolved in DMF (25 mL). After cooling to 5 °C, the substituted amine was added to the mixture and was stirred at room temperature overnight followed by evaporation under reduced pressure to remove DMF. The residue was purified by column chromatography (pet. ether/EtOAc 7:1 to 2:1) to afford 5 and 6 with the yields of 66percent and 84percent respectively.Step (v): Preparation of 5-formyI-2, 4-dimethyl-lH-pyrrole-3-carboxyIic acid(2-diethylaminoethyl)-amide (VII):Into a 10-L four necked round-bottomed flask equipped with a mechanical stirrer, a thermometer pocket, addition funnel and an air condenser were charged 5-formyl-2, 4- dimethyl- lH-pyrrole-3-carboxylic acid (0.25 Kg; 1.5 mole), tetrahydrofuran(3.5 L), dicyclohexyl carbodimide (0.432 Kg), 1 -hydroxy benzotriazole (0.306 Kg)and stirred well for 30 minutes. To this solution, a premixed solution of TEA (0.42 L) in tetrahydrofuran (1.25 L) and 2-diethylaminoethyl amine (0.286 L; 2.04 mole) in tetrahydrofuran (1.25 L) were added successively at 25-30° C. After addition, the reaction mixture was stirred for 16 hours at 25-30° C and the byproduct generated was removed by filtration through filtration funnel. The solvent was removed by distillation under diminished pressure. The resulting product was suspended in DM water and the pH of the slurry adjusted to 12-13 with aqueous NaOH solution. After pH adjustment, the product was extracted with ethyl acetate and washed successively organic layer with aqueous NaHCψInto a 10-L four necked round-bottomed flask equipped with a mechanical stirrer, a thermometer pocket, addition funnel and an air condenser were charged 5-formyl-2, 4-dimethyl-1H-pyrrole-3-carboxylic acid (0.25 Kg; 1.5 mole), tetrahydrofuran (3.5 L), dicyclohexyl carbodimide (0.432 Kg), 1-hydroxy benzotriazole (0.306 Kg) and stirred well for 30 minutes.

Molecular Weight:265.35
XLogP3:1.3
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:7
Exact Mass:265.17902698
Monoisotopic Mass:265.17902698
Topological Polar Surface Area:65.2
Heavy Atom Count:19
Complexity:305
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes