N-{1-[3-(2-ethoxyphenyl)-5-oxo-4,5-dihydro-[1,2,4]triazin-6-yl]ethyl}butyroamide
2-(2-ethoxy-phenyl)-5-methyl-7-propyl-3H-imidazo[5,1-f][1,2,4]triazin-4-one
Conditions | Yield |
---|---|
With trichlorophosphate In toluene for 2h; Reflux; | 78% |
With trichlorophosphate | |
With trichlorophosphate In 1,2-dichloro-ethane for 2h; Reflux; | |
With trichlorophosphate In 1,2-dichloro-ethane for 2h; Reflux; |
3-(2-ethoxy-benzoylamino)-5-methyl-2-propyl-3H-imidazole-4-carboxamide
2-(2-ethoxy-phenyl)-5-methyl-7-propyl-3H-imidazo[5,1-f][1,2,4]triazin-4-one
Conditions | Yield |
---|---|
With potassium tert-butylate In tert-butyl alcohol at 160℃; for 30h; | 72% |
With potassium tert-butylate In tert-butyl alcohol at 160℃; for 30h; Sealed tube; | 72% |
5-methyl-2-propyl-3H-imidazole-4-carboxamide
2-(2-ethoxy-phenyl)-5-methyl-7-propyl-3H-imidazo[5,1-f][1,2,4]triazin-4-one
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: lithium hexamethyldisilazane / dimethylformamide; tetrahydrofuran / 0.17 h / -10 °C 1.2: 41 percent / Ph2P(O)ONH2 / tetrahydrofuran; dimethylformamide / 20 °C 2.1: 52 percent / pyridine / 2 h / 60 °C 3.1: 72 percent / KOtBu / 2-methyl-propan-2-ol / 30 h / 160 °C View Scheme |
3-amino-5-methyl-2-propyl-3H-imidazole-4-carboxamide
2-(2-ethoxy-phenyl)-5-methyl-7-propyl-3H-imidazo[5,1-f][1,2,4]triazin-4-one
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 52 percent / pyridine / 2 h / 60 °C 2: 72 percent / KOtBu / 2-methyl-propan-2-ol / 30 h / 160 °C View Scheme |
ethyl 5-methyl-2-propyl-3H-imidazole-4-carboxylate
2-(2-ethoxy-phenyl)-5-methyl-7-propyl-3H-imidazo[5,1-f][1,2,4]triazin-4-one
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: 53 percent / ammonium hydroxide / 24 h / 130 °C 2.1: lithium hexamethyldisilazane / dimethylformamide; tetrahydrofuran / 0.17 h / -10 °C 2.2: 41 percent / Ph2P(O)ONH2 / tetrahydrofuran; dimethylformamide / 20 °C 3.1: 52 percent / pyridine / 2 h / 60 °C 4.1: 72 percent / KOtBu / 2-methyl-propan-2-ol / 30 h / 160 °C View Scheme |
2-butyrylaminopropionic acid
2-(2-ethoxy-phenyl)-5-methyl-7-propyl-3H-imidazo[5,1-f][1,2,4]triazin-4-one
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: Py; DMAP 2: POCl3 View Scheme | |
Multi-step reaction with 3 steps 1.1: dmap; pyridine / tetrahydrofuran / 4 h / Reflux 2.1: hydrazine hydrate / ethanol / 20 °C 2.2: 3.25 h / Reflux 3.1: trichlorophosphate / 1,2-dichloro-ethane / 2 h / Reflux View Scheme | |
Multi-step reaction with 3 steps 1: dmap; pyridine / tetrahydrofuran / 4 h / Reflux 2: ethanol / 3 h / Reflux 3: trichlorophosphate / 1,2-dichloro-ethane / 2 h / Reflux View Scheme |
2-ethoxybenzonitrile
2-(2-ethoxy-phenyl)-5-methyl-7-propyl-3H-imidazo[5,1-f][1,2,4]triazin-4-one
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: AlMeClNH2 2: N2H4 3: POCl3 View Scheme | |
Multi-step reaction with 3 steps 1.1: trimethylaluminum; ammonium chloride / toluene / 7 h / 0 - 80 °C 2.1: hydrazine hydrate / ethanol / 20 °C 2.2: 3.25 h / Reflux 3.1: trichlorophosphate / 1,2-dichloro-ethane / 2 h / Reflux View Scheme | |
Multi-step reaction with 4 steps 1.1: amino(methyl)aluminum chloride / toluene / 6 h / 80 °C 2.1: hydrazine hydrate / ethanol / 20 °C 2.2: Reflux 3.1: ethanol / 3 h / Reflux 4.1: trichlorophosphate / 1,2-dichloro-ethane / 2 h / Reflux View Scheme |
2-ethoxy-benzamidine hydrochloride
2-(2-ethoxy-phenyl)-5-methyl-7-propyl-3H-imidazo[5,1-f][1,2,4]triazin-4-one
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: N2H4 2: POCl3 View Scheme |
ethyl 3-butyramido-2-oxobutyrate
2-(2-ethoxy-phenyl)-5-methyl-7-propyl-3H-imidazo[5,1-f][1,2,4]triazin-4-one
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: POCl3 View Scheme | |
Multi-step reaction with 2 steps 1.1: hydrazine hydrate / ethanol / 20 °C 1.2: 3.25 h / Reflux 2.1: trichlorophosphate / 1,2-dichloro-ethane / 2 h / Reflux View Scheme | |
Multi-step reaction with 2 steps 1: ethanol / 3 h / Reflux 2: trichlorophosphate / 1,2-dichloro-ethane / 2 h / Reflux View Scheme |
2-ethoxybenzimidohydrazide
2-(2-ethoxy-phenyl)-5-methyl-7-propyl-3H-imidazo[5,1-f][1,2,4]triazin-4-one
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: POCl3 View Scheme | |
Multi-step reaction with 2 steps 1: ethanol / 3 h / Reflux 2: trichlorophosphate / 1,2-dichloro-ethane / 2 h / Reflux View Scheme |
ethyl 3-butyramido-2-oxobutyrate
2-(2-ethoxy-phenyl)-5-methyl-7-propyl-3H-imidazo[5,1-f][1,2,4]triazin-4-one
Conditions | Yield |
---|---|
Stage #1: C9H13N3O*ClH; ethyl 3-butyramido-2-oxobutyrate In ethanol at 70℃; for 4h; Stage #2: With trichlorophosphate In 1,2-dichloro-ethane for 2h; Heating / reflux; |
2-butyrylaminopropionic acid
2-ethoxy-benzamidine hydrochloride
Ethyl oxalyl chloride
2-(2-ethoxy-phenyl)-5-methyl-7-propyl-3H-imidazo[5,1-f][1,2,4]triazin-4-one
Conditions | Yield |
---|---|
With pyridine; sodium hydrogencarbonate; hydrazine hydrate; trichlorophosphate In tetrahydrofuran; ethanol; ethyl acetate; 1,2-dichloro-ethane | 4.00 g (28%) |
3-(2-ethoxyphenyl)-6-ethyl-4H-[1,2,4]triazin-5-one
2-(2-ethoxy-phenyl)-5-methyl-7-propyl-3H-imidazo[5,1-f][1,2,4]triazin-4-one
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 14 h / Reflux; Inert atmosphere 2.1: ammonia / tetrahydrofuran / 20 °C 3.1: tertiary amine / dichloromethane / 0.08 h / Cooling 3.2: 1.17 h / 0 - 20 °C 4.1: trichlorophosphate / toluene / 2 h / Reflux View Scheme |
6-(1-bromoethyl)-3-(2-ethoxyphenyl)-4H-[1,2,4]triazin-5-one
2-(2-ethoxy-phenyl)-5-methyl-7-propyl-3H-imidazo[5,1-f][1,2,4]triazin-4-one
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: ammonia / tetrahydrofuran / 20 °C 2.1: tertiary amine / dichloromethane / 0.08 h / Cooling 2.2: 1.17 h / 0 - 20 °C 3.1: trichlorophosphate / toluene / 2 h / Reflux View Scheme |
C13H16N4O2
2-(2-ethoxy-phenyl)-5-methyl-7-propyl-3H-imidazo[5,1-f][1,2,4]triazin-4-one
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: tertiary amine / dichloromethane / 0.08 h / Cooling 1.2: 1.17 h / 0 - 20 °C 2.1: trichlorophosphate / toluene / 2 h / Reflux View Scheme |
2-Ethoxybenzamidine
2-(2-ethoxy-phenyl)-5-methyl-7-propyl-3H-imidazo[5,1-f][1,2,4]triazin-4-one
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: hydrazine hydrate / ethanol / 20 °C 1.2: 3.25 h / Reflux 2.1: trichlorophosphate / 1,2-dichloro-ethane / 2 h / Reflux View Scheme | |
Multi-step reaction with 3 steps 1.1: hydrazine hydrate / ethanol / 20 °C 1.2: Reflux 2.1: ethanol / 3 h / Reflux 3.1: trichlorophosphate / 1,2-dichloro-ethane / 2 h / Reflux View Scheme |
2-(2-ethoxy-phenyl)-5-methyl-7-propyl-3H-imidazo[5,1-f][1,2,4]triazin-4-one
4-ethoxy-3-(5-methyl-4-oxo-7-propyl-3,4-dihydroimidazo[5,1-f][1,2,4]triazin-2-yl)-benzenelsulfonic acid chloride
Conditions | Yield |
---|---|
With chlorosulfonic acid at 0 - 20℃; | 91% |
With chlorosulfonic acid for 12h; Cooling with ice; | 76% |
With chlorosulphuric acid for 12h; Cooling with ice; | 76% |
2-(2-ethoxy-phenyl)-5-methyl-7-propyl-3H-imidazo[5,1-f][1,2,4]triazin-4-one
Conditions | Yield |
---|---|
With N-iodo-succinimide; trifluoroacetic acid at 0 - 20℃; | 79% |
With N-iodo-succinimide; trifluoroacetic acid at 0 - 20℃; | 79% |
With N-iodo-succinimide In trifluoroacetic acid at 0 - 20℃; | 71% |
With N-iodo-succinimide; trifluoroacetic acid at 0 - 20℃; |
2-(2-ethoxy-phenyl)-5-methyl-7-propyl-3H-imidazo[5,1-f][1,2,4]triazin-4-one
Conditions | Yield |
---|---|
Stage #1: 2-(2-ethoxy-phenyl)-5-methyl-7-propyl-3H-imidazo[5,1-f][1,2,4]triazin-4-one With pyridine; diphosphorus pentasulfide In toluene for 6h; Reflux; Stage #2: With ammonia; water In ethanol for 0.5h; Reflux; | 72% |
With pyridine; tetraphosphorus decasulfide for 6h; Reflux; | 72% |
4-ethylpiperazine
2-(2-ethoxy-phenyl)-5-methyl-7-propyl-3H-imidazo[5,1-f][1,2,4]triazin-4-one
vardenafil
Conditions | Yield |
---|---|
Stage #1: 2-(2-ethoxy-phenyl)-5-methyl-7-propyl-3H-imidazo[5,1-f][1,2,4]triazin-4-one With chlorosulfonic acid at 0 - 22℃; for 0.75h; Stage #2: 4-ethylpiperazine In dichloromethane at -3 - 25℃; for 0.75h; Product distribution / selectivity; |
4-ethylpiperazine
citric acid
2-(2-ethoxy-phenyl)-5-methyl-7-propyl-3H-imidazo[5,1-f][1,2,4]triazin-4-one
vardenafil citrate
Conditions | Yield |
---|---|
Stage #1: 2-(2-ethoxy-phenyl)-5-methyl-7-propyl-3H-imidazo[5,1-f][1,2,4]triazin-4-one With chlorosulfonic acid at -5 - 20℃; Stage #2: 4-ethylpiperazine With sodium hydroxide In tetrahydrofuran; water at 15℃; pH=9 - 9.5; Stage #3: citric acid In tetrahydrofuran at 50 - 70℃; |
2-(2-ethoxy-phenyl)-5-methyl-7-propyl-3H-imidazo[5,1-f][1,2,4]triazin-4-one
vardenafil
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: chlorosulfonic acid / -5 - 20 °C 1.2: 15 °C / pH 9 - 9.5 1.3: 50 - 70 °C 2.1: sodium hydroxide / water / pH 9 - 10 View Scheme | |
Multi-step reaction with 2 steps 1: chlorosulfonic acid / 0 - 5 °C 2: dichloromethane / 25 - 30 °C View Scheme |
2-(2-ethoxy-phenyl)-5-methyl-7-propyl-3H-imidazo[5,1-f][1,2,4]triazin-4-one
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: chlorosulfonic acid / -5 - 20 °C 1.2: 15 °C / pH 9 - 9.5 1.3: 50 - 70 °C 2.1: sodium hydroxide / water / pH 9 - 10 3.1: hydrogenchloride / water; acetone View Scheme | |
Multi-step reaction with 3 steps 1: chlorosulfonic acid / 0 - 5 °C 2: dichloromethane / 25 - 30 °C 3: hydrogenchloride; water / acetone View Scheme |
2-(2-ethoxy-phenyl)-5-methyl-7-propyl-3H-imidazo[5,1-f][1,2,4]triazin-4-one
2,2'-[(piperazine-1,4-disulfonyl)bis(2-ethoxy-5,1-phenylene)]-bis[5-methyl-7-propylimidazo[5,1-f][1,2,4]triazin-4(3H)-one]
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: chlorosulfonic acid / 0 - 5 °C 2: triethylamine / dichloromethane / 0.5 h / 25 - 30 °C View Scheme |
2-(2-ethoxy-phenyl)-5-methyl-7-propyl-3H-imidazo[5,1-f][1,2,4]triazin-4-one
N-{[4-ethoxy-3-(5-methyl-4-oxo-7-propyl-3,4-dihydroimidazo[5,1-f]-1,2,4-triazin-2-yl) phenyl]sulfonyl}glycene
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: chlorosulfonic acid / 0 - 5 °C 2.1: sodium hydroxide / water / 0.5 h / 25 - 30 °C 2.2: 2.5 h / 2 - 20 °C View Scheme |
2-(2-ethoxy-phenyl)-5-methyl-7-propyl-3H-imidazo[5,1-f][1,2,4]triazin-4-one
C19H26N6O4S
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: chlorosulfonic acid / 0 - 5 °C 2: dichloromethane / 1.33 h / 2 °C View Scheme |
2-(2-ethoxy-phenyl)-5-methyl-7-propyl-3H-imidazo[5,1-f][1,2,4]triazin-4-one
{[2-({[4-ethoxy-3-(5-methyl-4-oxo-7-propyl-3,4-dihydroimidazo[5,1-f]-1,2,4-triazin-2-yl)phenyl]sulfonyl}amino)ethyl]amino}(oxo)acetic acid
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: chlorosulfonic acid / 0 - 5 °C 2: dichloromethane / 1.33 h / 2 °C 3: triethylamine / 0.25 h / 25 - 30 °C 4: water; sodium hydroxide / methanol / 0.25 h / 25 °C View Scheme |
2-(2-ethoxy-phenyl)-5-methyl-7-propyl-3H-imidazo[5,1-f][1,2,4]triazin-4-one
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: chlorosulfonic acid / 0 - 5 °C 2: dichloromethane / 1.33 h / 2 °C 3: triethylamine / 0.25 h / 25 - 30 °C View Scheme |
2-(2-ethoxy-phenyl)-5-methyl-7-propyl-3H-imidazo[5,1-f][1,2,4]triazin-4-one
2-{2-ethoxy-5-[(4-ethyl-4-hydroxy-4λ5-piperazin-1-yl)sulfonyl]phenyl}-5-methyl-7-propyl imidazo-[5,1-f]-1,2,4-triazin-4(3H)-one N-oxide
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: chlorosulfonic acid / 0 - 5 °C 2: dichloromethane / 25 - 30 °C 3: peracetic acid / dichloromethane / 2 h / 0 - 5 °C View Scheme |
2-(2-ethoxy-phenyl)-5-methyl-7-propyl-3H-imidazo[5,1-f][1,2,4]triazin-4-one
2-{2-ethoxy-5-[(3-oxo-1-piperazinyl)sulfonyl]phenyl}-5-methyl-7-propylimidazo[5,1-f]-1,2,4-triazin-4(3H)-one
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: chlorosulfonic acid / 0 - 5 °C 2: dichloromethane / 0.5 h / 25 - 30 °C View Scheme |
2-(2-ethoxy-phenyl)-5-methyl-7-propyl-3H-imidazo[5,1-f][1,2,4]triazin-4-one
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: chlorosulfonic acid / dichloromethane / 24 h / 23 - 90 °C 2: dichloromethane 3: hydrogenchloride / water; acetone / 50 °C View Scheme |
Systematic Name: 2-(2-Ethoxyphenyl)-5-methyl-7-propylimidazo[5,1-f][1,2,4]triazin-4(1H)-one
SMILES: O=C2/N=C(\Nn1c(nc(c12)C)CCC)c3ccccc3OCC
InChI: InChI=1/C17H20N4O2/c1-4-8-14-18-11(3)15-17(22)19-16(20-21(14)15)12-9-6-7-10-13(12)23-5-2/h6-7,9-10H,4-5,8H2,1-3H3,(H,19,20,22)
InChIKey: YRRWQMBIMZMVDB-UHFFFAOYAC
Empirical Formula: C17H20N4O2
Molecular Weight: 312.3663
Nominal Mass: 312
Average Mass: 312.3663
Monoisotopic Mass: 312.158626
H bond acceptors: 6
H bond donors: 1
Freely Rotating Bonds: 5
Index of Refraction: 1.632
Molar Refractivity: 88.049 cm3
Molar Volume: 246.814 cm3
Surface Tension: 45.786 dyne/cm
Density: 1.266 g/cm3
Flash Point: 268.105 °C
Enthalpy of Vaporization: 79.252 kJ/mol
Boiling Point: 519.699 °C at 760 mmHg
Vapour Pressure: 0 mmHg at 25 °C
Appearance: Pale Yellow Solid
Melting Point: 198-200 °C
Product Categories of 2-(2-Ethoxyphenyl)-5-methyl-7-propyl-3H-imidazo[5,1-f][1,2,4]triazin-4-one (CAS NO.224789-21-3): Heterocyclic Compounds; Heterocycles; Intermediates & Fine Chemicals; Pharmaceuticals
2-(2-Ethoxyphenyl)-5-methyl-7-propyl-3H-imidazo[5,1-f][1,2,4]triazin-4-one (CAS NO.224789-21-3) is used as vardenafil intermediate.
2-(2-Ethoxyphenyl)-5-methyl-7-propyl-3H-imidazo[5,1-f][1,2,4]triazin-4-one (CAS NO.224789-21-3), its Synonyms are 2-(2-Ethoxyphenyl)-5-methyl-7-propylimidazo[5,1-f][1,2,4]triazin-4-ol ; Imidazo[5,1-f][1,2,4]triazin-4(1H)-one, 2-(2-ethoxyphenyl)-5-methyl-7-propyl- ; 2-(2-Ethoxyphenyl)-5-methyl-7-propylimidazo[5,1-f][1,2,4]triazin-4(3H)-one .
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