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

Name
N-(2-(Diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide
EINECS 807-829-4
CAS No. 356068-86-5
Article Data30
CAS DataBase
Density 1.096 g/cm³
Solubility
Melting Point
Formula C₁₄H₂₃N₃O₂
Boiling Point 389.9 °C at 760 mmHg
Molecular Weight 265.356
Flash Point 189.6 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 5-Formyl-2,4-dimethyl-1H-pyrrole-3-carboxylicacid (2-diethylamino-ethyl)-amide;1H-Pyrrole-3-carboxamide, N-[2-(diethylamino)ethyl]-5-formyl-2,4-dimethyl-;
PSA 65.20000
LogP 1.90650

Synthetic route

: 5-[(2-diethylamino-ethylimino)-methyl]-2,4-dimethyl-1H-pyrrole-3-carboxylic acid (2-diethylamino-ethyl)-amide

: 356068-86-5
N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide

Conditions

Conditions	Yield
With water	100%

: 253870-02-9
5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxylic acid

: 100-36-7
N,N-diethylethylenediamine

: 356068-86-5
N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane; N,N-dimethyl-formamide at 0 - 20℃; for 59h;	86.3%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide	84%
Stage #1: 5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxylic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 0.333333h; Stage #2: N,N-diethylethylenediamine With triethylamine In N,N-dimethyl-formamide at 20℃;	80%

: 253870-02-9
5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxylic acid

: 616-40-0
N,N-diethylhydrazine

: 356068-86-5
N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane; N,N-dimethyl-formamide at 0 - 20℃; for 59h;	86.3%

: 253870-02-9
5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxylic acid

1-(3-dimethyl-aminopropyl-3-ethylcarbodiimide hydrochloride: 1-(3-dimethyl-aminopropyl-3-ethylcarbodiimide hydrochloride

: 2592-95-2
benzotriazol-1-ol

: 100-36-7
N,N-diethylethylenediamine

: 356068-86-5
N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide

Conditions

Conditions	Yield
With sodium hydroxide; triethylamine In N-methyl-acetamide; methanol; dichloromethane; water; ethyl acetate; toluene	43%
With sodium hydroxide; triethylamine In N-methyl-acetamide; methanol; dichloromethane; water; ethyl acetate; toluene	43%
With sodium hydroxide; triethylamine In N-methyl-acetamide; methanol; dichloromethane; water; ethyl acetate; toluene	43%

...Expand

: 253870-02-9
5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxylic acid

: 356068-86-5
N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: tetrahydrofuran / 45 °C 2: imidazole / carbon dioxide / tetrahydrofuran / 45 °C 3: 100 percent / H2O View Scheme

: 452105-37-2
4-(imidazole-1-carbonyl)-3,5-dimethyl-1H-pyrrole-2-carbaldehyde

: 356068-86-5
N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: imidazole / carbon dioxide / tetrahydrofuran / 45 °C 2: 100 percent / H2O View Scheme

: 2199-59-9
ethyl (5-formyl-2,4-dimethyl-1H-pyrrole)-3-carboxylate

: 356068-86-5
N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 90 percent / aq. KOH / methanol / 3 h / Heating 2: 50 percent / EDC; HOBt; Et3N / dimethylformamide / 20 °C View Scheme
Multi-step reaction with 2 steps 1.1: potassium hydroxide; water / methanol / 4 - 6 h / 60 - 70 °C 2.1: dicyclohexyl-carbodiimide; benzotriazol-1-ol / tetrahydrofuran / 0.5 h 2.2: 16 h / 25 - 30 °C View Scheme
Multi-step reaction with 2 steps 1: water; potassium hydroxide / methanol / 3 h / Reflux 2: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / 12 h / 20 °C View Scheme

: 86770-31-2
2-tert-butyl 4-ethyl 3,5-dimethyl-1H-pyrrole-2,4-dicarboxylate

: 356068-86-5
N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 81 percent / TFA / -5 - 20 °C 2: 90 percent / aq. KOH / methanol / 3 h / Heating 3: 50 percent / EDC; HOBt; Et3N / dimethylformamide / 20 °C View Scheme
Multi-step reaction with 4 steps 1.1: hydrogenchloride / isopropyl alcohol / 25 - 50 °C 2.1: trichlorophosphate / 2 - 3 h / 0 - 50 °C 2.2: 25 - 30 °C / pH 12 - 13 3.1: potassium hydroxide; water / methanol / 4 - 6 h / 60 - 70 °C 4.1: dicyclohexyl-carbodiimide; benzotriazol-1-ol / tetrahydrofuran / 0.5 h 4.2: 16 h / 25 - 30 °C View Scheme
Multi-step reaction with 4 steps 1: hydrogenchloride; water / ethanol / 3 h / 70 °C 2: trichlorophosphate / 1,2-dichloro-ethane / 2 h / Reflux 3: water; potassium hydroxide / methanol / 3 h / Reflux 4: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / 12 h / 20 °C View Scheme
Multi-step reaction with 4 steps 1: hydrogenchloride / ethanol; water / 1 h / 60 °C 2: trichlorophosphate / dichloromethane / 2 h / Reflux 3: potassium hydroxide / methanol; water / 4 h / Reflux 4: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; triethylamine / N,N-dimethyl-formamide View Scheme

: 253870-02-9
5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxylic acid

: 100-36-7
N,N-diethylethylenediamine

A 5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxylic acid (2-diethylarnino-ethyl)-amide: 5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxylic acid (2-diethylarnino-ethyl)-amide

B: 356068-86-5
N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide

Conditions

Conditions	Yield
	A 6.19g (78%) B n/a

...Expand

: 2199-51-1
2,4-dimethyl-1H-pyrrole-3-carboxylic acid ethyl ester

: 356068-86-5
N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: trichlorophosphate / 2 - 3 h / 0 - 50 °C 1.2: 25 - 30 °C / pH 12 - 13 2.1: potassium hydroxide; water / methanol / 4 - 6 h / 60 - 70 °C 3.1: dicyclohexyl-carbodiimide; benzotriazol-1-ol / tetrahydrofuran / 0.5 h 3.2: 16 h / 25 - 30 °C View Scheme
Multi-step reaction with 3 steps 1: trichlorophosphate / 1,2-dichloro-ethane / 2 h / Reflux 2: water; potassium hydroxide / methanol / 3 h / Reflux 3: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / 12 h / 20 °C View Scheme
Multi-step reaction with 3 steps 1.1: trichlorophosphate / dichloromethane / 1.5 h / Reflux 1.2: 0.5 h / Reflux 2.1: sodium hydroxide; water / methanol / 4.5 h / 82 - 83 °C / Inert atmosphere 3.1: dicyclohexyl-carbodiimide; dmap / dichloromethane; N,N-dimethyl-formamide / 59 h / 0 - 20 °C View Scheme
Multi-step reaction with 3 steps 1: trichlorophosphate / dichloromethane / 2 h / Reflux 2: potassium hydroxide / methanol; water / 4 h / Reflux 3: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; triethylamine / N,N-dimethyl-formamide View Scheme
Multi-step reaction with 3 steps 1.1: trichlorophosphate / dichloromethane / 0.5 h / 0 °C 1.2: 1.5 h / Reflux 2.1: sodium hydroxide / water; methanol / 4.5 h / Reflux; Inert atmosphere 3.1: dicyclohexyl-carbodiimide; dmap / dichloromethane; N,N-dimethyl-formamide / 59 h / 0 - 20 °C View Scheme

: 2436-79-5
diethyl 2,4-dimethylpyrrole-3,5-dicarboxylate

: 356068-86-5
N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: water; potassium hydroxide / ethanol / 10 h / 50 - 60 °C 2.1: Inert atmosphere 3.1: trichlorophosphate / dichloromethane / 1.5 h / Reflux 3.2: 0.5 h / Reflux 4.1: sodium hydroxide; water / methanol / 4.5 h / 82 - 83 °C / Inert atmosphere 5.1: dicyclohexyl-carbodiimide; dmap / dichloromethane; N,N-dimethyl-formamide / 59 h / 0 - 20 °C View Scheme
Multi-step reaction with 5 steps 1.1: potassium hydroxide / ethanol; water / 10 h / 50 °C 2.1: 0.08 h / 200 °C / Inert atmosphere 3.1: trichlorophosphate / dichloromethane / 0.5 h / 0 °C 3.2: 1.5 h / Reflux 4.1: sodium hydroxide / water; methanol / 4.5 h / Reflux; Inert atmosphere 5.1: dicyclohexyl-carbodiimide; dmap / dichloromethane; N,N-dimethyl-formamide / 59 h / 0 - 20 °C View Scheme

: 5442-91-1
3,5-dimethyl-1H-pyrrole-2,4-dicarboxylic acid 4-ethyl ester

: 356068-86-5
N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: Inert atmosphere 2.1: trichlorophosphate / dichloromethane / 1.5 h / Reflux 2.2: 0.5 h / Reflux 3.1: sodium hydroxide; water / methanol / 4.5 h / 82 - 83 °C / Inert atmosphere 4.1: dicyclohexyl-carbodiimide; dmap / dichloromethane; N,N-dimethyl-formamide / 59 h / 0 - 20 °C View Scheme
Multi-step reaction with 4 steps 1.1: 0.08 h / 200 °C / Inert atmosphere 2.1: trichlorophosphate / dichloromethane / 0.5 h / 0 °C 2.2: 1.5 h / Reflux 3.1: sodium hydroxide / water; methanol / 4.5 h / Reflux; Inert atmosphere 4.1: dicyclohexyl-carbodiimide; dmap / dichloromethane; N,N-dimethyl-formamide / 59 h / 0 - 20 °C View Scheme

: 68-12-2, 33513-42-7
N,N-dimethyl-formamide

: 590424-05-8
N-(2-(diethylamino)ethyl)-2,4-dimethyl-1H-pyrrole-3-carboxamide

: 356068-86-5
N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide

Conditions

Conditions	Yield
Stage #1: N,N-dimethyl-formamide With oxalyl dichloride In dichloromethane at 0 - 10℃; for 2.5h; Inert atmosphere; Stage #2: N-[2-(diethylamino)ethyl]-2,4-dimethyl-1H-pyrrole-3-carboxamide In dichloromethane at 30℃;

: 590424-04-7
tert-butyl 4-[[[2-(diethylamino)ethyl]amino]carbonyl]-3,5-dimethyl-1H-pyrrole-2-carboxylate

: 356068-86-5
N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sulfuric acid / water; methanol / 3.5 h / 60 - 65 °C 2.1: oxalyl dichloride / dichloromethane / 2.5 h / 0 - 10 °C / Inert atmosphere 2.2: 30 °C View Scheme

: 100-36-7
N,N-diethylethylenediamine

: 356068-86-5
N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: dichloromethane / 0.5 h / 0 - 20 °C 2.1: zinc / methanol; acetic acid / 65 - 70 °C 3.1: sulfuric acid / water; methanol / 3.5 h / 60 - 65 °C 4.1: oxalyl dichloride / dichloromethane / 2.5 h / 0 - 10 °C / Inert atmosphere 4.2: 30 °C View Scheme

: 590424-03-6
N-(2-(diethylamino)ethyl)-3-oxobutanamide

: 356068-86-5
N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: zinc / methanol; acetic acid / 65 - 70 °C 2.1: sulfuric acid / water; methanol / 3.5 h / 60 - 65 °C 3.1: oxalyl dichloride / dichloromethane / 2.5 h / 0 - 10 °C / Inert atmosphere 3.2: 30 °C View Scheme

: 56341-41-4
5-fluoroindol-2(3H)-one

: 356068-86-5
N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide

: 557795-19-4
sunitinib

Conditions

Conditions	Yield
With piperidine In toluene for 3h; Solvent; Reagent/catalyst; Knoevenagel Condensation; Reflux;	97.3%
With piperidine In toluene for 3h; Reagent/catalyst; Solvent; Reflux;	97.3%
With potassium hydroxide In N,N-dimethyl-formamide at 20℃; for 3.5h; Aldol Condensation; Darkness; Inert atmosphere;	94%

: 20870-78-4
5-bromo-2-indolin-2-one

: 356068-86-5
N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide

: 5-(5-Bromo-2-oxo-1,2-dihydroindol-3-ylidenemethyl)-2,4-dimethyl-1H-pyrrole-3-carboxylic acid (2-diethylamino-ethyl)amide

Conditions

Conditions	Yield
With piperidine In ethanol at 90℃; for 6h; Knoevenagel condensation;	96%
	0.09 g (26%)
	0.09 g (26%)
With piperidine In ethanol at 80℃; for 1h;	368 mg

: C43H37Br2NP2

: 356068-86-5
N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide

: C35H51N7O2

Conditions

Conditions	Yield
Stage #1: C43H37Br2NP2 With n-butyllithium In tetrahydrofuran at -75℃; for 0.5h; Stage #2: N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide In tetrahydrofuran for 2h;	91%

: 356068-86-5
N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide

: N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide-α-d1

Conditions

Conditions	Yield
With 1,3-bis-(2,4,6-trimethylphenyl)-4,5-dihydro-3H-imidazol-1-ium bromide; water-d2; potassium carbonate In dichloromethane at 80℃; for 12h;	88%

: 97-67-6
(S)-Malic acid

: 356068-86-5
N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide

: 1200435-83-1
L-(-)-malic acid of 5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxylic acid (2-diethylaminoethyl)amide

Conditions

Conditions	Yield
In dichloromethane at 25 - 30℃;	86%
In butan-1-ol at 57℃;

: 56341-41-4
5-fluoroindol-2(3H)-one

: 97-67-6
(S)-Malic acid

: 356068-86-5
N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide

: sunitinib L-malate

Conditions

Conditions	Yield
Stage #1: 5-fluoroindol-2(3H)-one; N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide With pyrrolidine In ethanol for 1.5h; Reflux; Stage #2: (S)-Malic acid In ethanol Product distribution / selectivity;	84%

...Expand

: 24424-99-5
di-tert-butyl dicarbonate

: 356068-86-5
N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide

: tert-butyl-3-[(tert-butoxycarbonyl)(2-(diethylamino)ethyl)carbamoyl]-5-formyl-2,4-dimethyl-1H-pyrrole-1-carboxylate

Conditions

Conditions	Yield
Stage #1: N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide With dmap In dichloromethane at 20℃; for 0.166667h; Stage #2: di-tert-butyl dicarbonate In dichloromethane at 20℃; for 50h;	84%

: 56341-41-4
5-fluoroindol-2(3H)-one

: 97-67-6
(S)-Malic acid

: 356068-86-5
N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide

: 341031-54-7
sunitinib malate

Conditions

Conditions	Yield
With pyrrolidine In ethanol at 78℃; for 3h;	80%
With pyrrolidine In ethanol at 78℃; for 3h;	80%
Stage #1: (S)-Malic acid; N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide In butan-1-ol at 48℃; Stage #2: 5-fluoroindol-2(3H)-one With pyrrolidine In butan-1-ol at 94℃; Product distribution / selectivity;	71.2%
Stage #1: 5-fluoroindol-2(3H)-one; N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide In ethanol at 8 - 10℃; Reflux; Stage #2: (S)-Malic acid In ethanol for 4 - 6h; Product distribution / selectivity; Reflux;	71%
Stage #1: (S)-Malic acid; N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide In tetrahydrofuran for 4 - 6h; Stage #2: 5-fluoroindol-2(3H)-one In tetrahydrofuran for 4 - 6h; Product distribution / selectivity; Reflux;

...Expand

: 56341-41-4
5-fluoroindol-2(3H)-one

: 2-(N,N-diethylamino)ethyl ammonium di(L-malate)

: 356068-86-5
N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide

: 341031-54-7
sunitinib malate

Conditions

Conditions	Yield
In methanol; acetonitrile at 25 - 30℃; for 3h;	80%

...Expand

: 56341-41-4
5-fluoroindol-2(3H)-one

: 97-67-6
(S)-Malic acid

: 356068-86-5
N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide

: N-[2-(diethylamino)ethyl]-5-[(Z)-(5-fluoro-1,2-dihydro-2-oxo-3H-indol-3-ylidene)methyl]-2,4-dimethyl-1H-pyrrole-3-carboxamide L-malate

Conditions

Conditions	Yield
Stage #1: 5-fluoroindol-2(3H)-one; N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide With pyrrolidine In ethanol at 78℃; for 1.5h; Stage #2: (S)-Malic acid In ethanol at 78℃; for 1h;	80%

...Expand

: 356068-86-5
N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide

: 1338703-87-9
C14H24N3O5S(1-)*Na(1+)

Conditions

Conditions	Yield
With sodium hydrogensulfite In ethanol; water at 10 - 20℃;	79%

: 110-89-4
piperidine

: 442562-94-9
4-(3-methoxy-phenyl)-1,3-dihydro-indol-2-one

: 356068-86-5
N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide

: 5-[4-(3-Methoxy-phenyl)-2-oxo-1,2-dihydro-indol-3-ylidenemethyl]-2,4-dimethyl-1 H-pyrrole-3-carboxylic acid (2-diethylaminoethyl)-amide

Conditions

Conditions	Yield
In ethanol	78%

...Expand

: 5-hydroxy-4,6-dimethyl-1H-pyrrolo[2,3-b]pyridin-2(3H)-one

: 356068-86-5
N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide

: (Z)-N-(2-(diethylamino)ethyl)-5-((5-hydroxy-4,6-dimethyl-2-oxo-1H-pyrrolo[2,3-b]pyridin-3(2H)-ylidene)methyl)-2,4-dimethyl-1H-pyrrole-3-carboxamide

Conditions

Conditions	Yield
With piperidine In ethanol for 20h; Knoevenagel Condensation; Reflux;	77%

: 193354-13-1
5-iodo-1,3-dihydro-indol-2-one

: 356068-86-5
N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide

: 1372783-13-5
N-[2-(diethylamino)ethyl]-5-[(Z)-(5-iodo-1,2-dihydro-2-oxo-3H-indole-3-ylidine)methyl]-2,4-dimethyl-1H-pyrrole-3-carboxamide

Conditions

Conditions	Yield
With piperidine In ethanol at 90℃; for 5h; Knoevenagel condensation;	76%

: 56341-41-4
5-fluoroindol-2(3H)-one

: 64-19-7
acetic acid

: 356068-86-5
N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide

: 1221149-36-5
sunitinib acetate

Conditions

Conditions	Yield
Stage #1: 5-fluoroindol-2(3H)-one; N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide With pyrrolidine In butan-1-ol at 20℃; Reflux; Stage #2: acetic acid In butan-1-ol Reflux;	75.3%

...Expand

: 56341-41-4
5-fluoroindol-2(3H)-one

: 2689-91-0, 4601-92-7, 5972-71-4, 6283-27-8, 18841-14-0, 18841-15-1, 20261-05-6, 54944-40-0, 85273-27-4, 85273-28-5, 102607-29-4
L-malic acid ; ammonium-L malate

: 356068-86-5
N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide

: 341031-54-7
sunitinib malate

Conditions

Conditions	Yield
In methanol; acetonitrile at 25 - 30℃; for 3h;	75%

...Expand

: 56341-41-4
5-fluoroindol-2(3H)-one

: di-(n-propyl ammonium) L-malate

: 356068-86-5
N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide

: 341031-54-7
sunitinib malate

Conditions

Conditions	Yield
In methanol; acetonitrile at 25 - 30℃; for 3h;	75%

...Expand

: 56341-37-8
6-chloro-2-oxindole

: 356068-86-5
N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide

: (Z)-5-((6-chloro-2-oxoindolin-3-ylidene)methyl)-N-(2-(diethylamino)ethyl)-2,4-dimethyl-1H-pyrrole-3-carboxamide

Conditions

Conditions	Yield
With pyrrolidine In ethanol for 3h; Reflux;	74%

: 56341-41-4
5-fluoroindol-2(3H)-one

: di-(diisopropyl ammonium) L-malate

: 356068-86-5
N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide

: 341031-54-7
sunitinib malate

Conditions

Conditions	Yield
In methanol; acetonitrile at 25 - 30℃; for 3h;	72.5%

...Expand

: 110-89-4
piperidine

: 442562-93-8
4-(4-methoxy-phenyl)-1,3-dihydro-indol-2-one

: 356068-86-5
N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide

: 5-[4-(4-methoxy-phenyl)-2-oxo-1,2-dihydro-indol-3-ylidenemethyl]-2,4-dimethyl-1 H-pyrrole-3-carboxylic acid (2-diethylamino-ethyl)-amide

Conditions

Conditions	Yield
In ethanol	72%

...Expand

: 56341-41-4
5-fluoroindol-2(3H)-one

: 1332307-07-9
2-(N,N-diethylamino)ethyl ammonium L-malate

: 356068-86-5
N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide

: 341031-54-7
sunitinib malate

Conditions

Conditions	Yield
In methanol; acetonitrile at 25 - 30℃; for 3h;	72%

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: 110-89-4
piperidine

: 442562-87-0
4-(4-fluoro-phenyl)-1,3-dihydro-indol-2-one

: 356068-86-5
N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide

: 5-[4-(4-Fluoro-phenyl)-2-oxo-1,2-dihydro-indol-3-ylidenemethyl]-2,4-dimethyl-1 H-pyrrole-3-carboxylic acid (2-diethylamino-ethyl)-amide

Conditions

Conditions	Yield
In ethanol	70%

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: 97-67-6
(S)-Malic acid

: 1374685-40-1
5-fluoro-1-(trimethylsilyl)-2-(trimethylsilyloxy)-1H-indole

: 356068-86-5
N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide

: 341031-54-7
sunitinib malate

Conditions

Conditions	Yield
Stage #1: 5-fluoro-1-(trimethylsilyl)-2-(trimethylsilyloxy)-1H-indole; N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide; trimethylsilyl trifluoromethanesulfonate In acetonitrile for 13h; Reflux; Stage #2: (S)-Malic acid In methanol; acetonitrile at 20℃; for 22h;	70%
Stage #1: 5-fluoro-1-(trimethylsilyl)-2-(trimethylsilyloxy)-1H-indole; N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide With trimethylsilyl trifluoromethanesulfonate In acetonitrile for 13h; Reflux; Stage #2: (S)-Malic acid In methanol for 24h;
Stage #1: 5-fluoro-1-(trimethylsilyl)-2-(trimethylsilyloxy)-1H-indole; N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide With trimethylsilyl trifluoromethanesulfonate In acetonitrile for 9.5h; Reflux; Stage #2: (S)-Malic acid In methanol for 24h;

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: 5-(2-azidoethyl)indolin-2-one

: 356068-86-5
N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide

: (Z)-5-((5-(2-azidoethyl)-2-oxoindolin-3-ylidene)methyl)-N-(2-(diethylamino)ethyl)-2,4-dimethyl-1H-pyrrole-3-carboxamide

Conditions

Conditions	Yield
With pyrrolidine In ethanol for 3h; Reflux;	68%

: 110-89-4
piperidine

: 442562-92-7
4-(3-bromo-phenyl)-1,3-dihydro-indol-2-one

: 356068-86-5
N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide

A 5-l4-(3-Bromophenyl)-2-oxo-1,2-dihydro-indol-3-ylidenemethyl]-2,4-dimethyl-1 H-pyrrole-3-carboxylic acid (2-diethylamino-ethyl)-amide: 5-l4-(3-Bromophenyl)-2-oxo-1,2-dihydro-indol-3-ylidenemethyl]-2,4-dimethyl-1 H-pyrrole-3-carboxylic acid (2-diethylamino-ethyl)-amide

B: 5-[4-(3-bromo-phenyl)-2-oxo-1,2-dihydro-indol-3-ylidenemethyl]-2,4-dimethyl-1 H-pyrrole-3-carboxylic acid (2-diethylamino-ethyl)-amide

Conditions

Conditions	Yield
In ethanol	A 67% B n/a

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: 134682-54-5
5-azaindolin-2-one

: 356068-86-5
N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide

: 1350702-94-1
(Z)-N-(2-(diethylamino)ethyl)-2,4-dimethyl-5-((2-oxo-1H-pyrrolo[3,2-c]pyridin-3(2H)-ylidene)methyl)-1H-pyrrole-3-carboxamide

Conditions

Conditions	Yield
With piperidine In methanol for 5h; Reflux;	62%

: N-(2-(2-oxoindolin-5-yl)ethyl)acetamide

: 356068-86-5
N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide

: (Z)-5-((5-(2-acetamidoethyl)-2-oxoindolin-3-ylidene)methyl)-N-(2-(diethylamino)ethyl)-2,4-dimethyl-1H-pyrrole-3-carboxamide

Conditions

Conditions	Yield
With pyrrolidine In ethanol for 3h; Reflux;	62%

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

The systematic name of N-(2-(Diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide is N-[2-(diethylamino)ethyl]-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide. With the CAS registry number 356068-86-5, it is also named as 1H-Pyrrole-3-carboxamide, N-[2-(diethylamino)ethyl]-5-formyl-2,4-dimethyl-. In addition, its molecular formula is C₁₄H₂₃N₃O₂ and molecular weight is 265.35.

The other characteristics of N-(2-(Diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide can be summarized as: (1)ACD/LogP: 1.61; (2)# of Rule of 5 Violations: 0; (3)ACD/BCF (pH 5.5): 1; (4)ACD/BCF (pH 7.4): 1; (5)ACD/KOC (pH 5.5): 1; (6)ACD/KOC (pH 7.4): 1.06; (7)#H bond acceptors: 5; (8)#H bond donors: 2; (9)#Freely Rotating Bonds: 7; (10)Polar Surface Area: 65.2 Å²; (11)Index of Refraction: 1.554; (12)Molar Refractivity: 77.59 cm³; (13)Molar Volume: 242.1 cm³; (14)Polarizability: 30.76×10^-24cm³; (15)Surface Tension: 44.4 dyne/cm; (16)Density: 1.096 g/cm³; (17)Flash Point: 189.6 °C; (18)Enthalpy of Vaporization: 63.93 kJ/mol; (19)Boiling Point: 389.9 °C at 760 mmHg; (20)Vapour Pressure: 2.75E-06 mmHg at 25 °C.

People can use the following data to convert to the molecule structure.
(1)SMILES: Cc1c(C(=O)NCCN(CC)CC)c(C)nc1C=O
(2)InChI: InChI=1/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)
(3)InChIKey: BRZYBFNUINXZMJ-UHFFFAOYAD
(4)Std. 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)
(5)Std. InChIKey: BRZYBFNUINXZMJ-UHFFFAOYSA-N

Product Name

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

Synthetic route

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

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