N-(2-(Diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide Chemical Properties

Melting point:

145-148°C

Boiling point:

389.9±42.0 °C(Predicted)

Density 

1.096

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

solubility 

Dichloromethane (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)

form 

Solid

pka

15.07±0.50(Predicted)

color 

Off-White

InChI

InChI=1S/C14H23N3O2/c1-5-17(6-2)8-7-15-14(19)13-10(3)12(9-18)16-11(13)4/h9,16H,5-8H2,1-4H3,(H,15,19)

InChIKey

BRZYBFNUINXZMJ-UHFFFAOYSA-N

SMILES

N1C(C=O)=C(C)C(C(NCCN(CC)CC)=O)=C1C

Safety Information

HS Code 

2933998090

N-(2-(Diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide Usage And Synthesis

Uses

N-[2-(Diethylamino)ethyl]-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide is used in the preparation of (pyrrolylmethylidene)indolinones as tyrosine kinase inhibitors.

Synthesis

To a three-necked flask fitted with a thermometer was added 5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxylic acid (3, 5.50 g, 32.7 mmol) and anhydrous DMF (13.1 mL), and cooled in an ice-salt bath to 0°C. Under stirring, a dichloromethane (78.4 mmol) solution of dicyclohexylcarbodiimide (DCC, 10.13 g, 49.0 mmol) was slowly added dropwise. mL) solution, keeping the reaction temperature between 0-2°C. Subsequently, 4-dimethylaminopyridine (DMAP, 1.65 g) and N1,N1-diethylethane-1,2-diamine (4, 5.03 mL, 35.9 mmol) were added and reacted at room temperature. The reaction progression was monitored by TLC (eluent: chloroform/methanol, v/v = 5:1). 59 h later, the reaction mixture was filtered, water was added to the filtrate, and extracted with dichloromethane (15 mL × 3). The organic layers were combined, washed with saturated brine (65.7 mL) and dried over anhydrous sodium sulfate. The filtrate was concentrated to give a solid, which was dissolved in a small amount of dichloromethane (5.0 mL). The resulting organic phase was washed with 5.0% aqueous citric acid (330 mL × 3) until TLC showed no product in the organic layer. The aqueous phase was alkalized to pH 8 with saturated aqueous sodium hydroxide and a large amount of aqueous sodium bicarbonate and extracted with dichloromethane (330 mL × 3). The organic layers were combined and concentrated to give a brown-red oily liquid. Further purification by column chromatography (eluent: petroleum ether/ethyl acetate, v/v = 3:1 to 1:1) afforded N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide (10, 8.11 g, 86.3%) as a yellowish solid with a melting point of 153-154 °C (literature value 177-181 °C). Yield 42.5%. rf = 0.60 (eluent: chloroform/methanol, v/v = 5:1). 1H NMR (400 MHz, DMSO-d6) δ: 11.85 (s, 1H, NH), 9.54 (s, 1H, CHO), 7.36-7.38 (t, 1H, CONH), 3.24-3.29 (m, 2H, NHCH2) , 2.50-2.56 (m, 6H, 3 × N-CH2), 2.32 (s, 3H, 4-CH3), 2.37 (s, 3H, 2-CH3), 0.95-0.99 (t, 6H, 2 × CH3).

References

[1] Research on Chemical Intermediates, 2015, vol. 41, # 11, p. 8941 - 8954

N-(2-(Diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide(356068-86-5)Related Product Information

• N-ethyl-pyrrolidone
• N-(2-Hydroxyethyl)-2-pyrrolidone
• N-[2-(DiethylaMino)ethyl]-2,4-diMethyl-1H-pyrrole-3-CarboxaMide
• De-5-fluoro 4-FluorochidaMide
• 2,4-DIMETHYL PYRROL-3-CARBALDEHYDE
• Ethyl 5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxylate
• 5-Fluoro-2-oxindole
• Pyrrole-2,4-dicarboxaldehyde, 3,5-dimethyl- (6CI,7CI,8CI)
• Sunitinib iMpurity
• Sunitinib Malate
• Ethyl 2,4-dimethyl-1H-pyrrole-3-carboxylate
• N-Desethyl Sunitinib
• 5-Formyl-2,4-dimethyl-1H-pyrrole-3-carboxylic acid
• (Z)-5-((5-fluoro-2-oxoindolin-3-ylidene)Methyl)-2,4-diMethyl-1H-pyrrole-3-carboxaMide
• Sunitinib Impurity 7
• Sunitinib Impurity 2
• Sunitinib Impurity 9
• Sunitinib Impurity 1