chloroacetyl chloride
5H-benzo[e]pyrido[3,2-b][1,4]diazepin-6(11H)-one
11-(chloroacetyl)-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one
Conditions | Yield |
---|---|
With triethylamine In 1,4-dioxane for 8h; Heating; | 70% |
With triethylamine In 1,4-dioxane for 8h; Heating; | 53% |
With triethylamine In 1,4-dioxane for 5h; Heating; |
ortho-nitrobenzoic acid
11-(chloroacetyl)-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: oxalyl chloride; DMF / tetrahydrofuran / 1 h / Heating 2: 5.55 g / pyridine / tetrahydrofuran / 2 h / 20 °C 3: 86 percent / aq. HCl; SnCl2 / 0.25 h / 100 °C 4: 80 percent / 0.08 h / 205 °C 5: 70 percent / Et3N / dioxane / 8 h / Heating View Scheme | |
Multi-step reaction with 5 steps 1: thionyl chloride / toluene / 2 h / Reflux 2: triethylamine / dichloromethane / 1 h / 15 - 30 °C 3: acetic acid; iron / ethanol / 3 h / 60 - 70 °C 4: potassium iodide / toluene / 3 h / Reflux 5: triethylamine / toluene / 2 h / 15 - 25 °C View Scheme |
2-amino-N-(2-chloropyridin-3-yl)benzamide
11-(chloroacetyl)-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 80 percent / 0.08 h / 205 °C 2: 70 percent / Et3N / dioxane / 8 h / Heating View Scheme | |
Multi-step reaction with 2 steps 1: 0.08 h / 210 °C 2: 53 percent / triethylamine / dioxane / 8 h / Heating View Scheme |
N-(2-chloro-pyridin-3-yl)-2-nitro-benzamide
11-(chloroacetyl)-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 86 percent / aq. HCl; SnCl2 / 0.25 h / 100 °C 2: 80 percent / 0.08 h / 205 °C 3: 70 percent / Et3N / dioxane / 8 h / Heating View Scheme | |
Multi-step reaction with 3 steps 1: acetic acid; iron / ethanol / 3 h / 60 - 70 °C 2: potassium iodide / toluene / 3 h / Reflux 3: triethylamine / toluene / 2 h / 15 - 25 °C View Scheme |
2-nitrobenzyl chloride
11-(chloroacetyl)-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 5.55 g / pyridine / tetrahydrofuran / 2 h / 20 °C 2: 86 percent / aq. HCl; SnCl2 / 0.25 h / 100 °C 3: 80 percent / 0.08 h / 205 °C 4: 70 percent / Et3N / dioxane / 8 h / Heating View Scheme | |
Multi-step reaction with 4 steps 1: triethylamine / dichloromethane / 1 h / 15 - 30 °C 2: acetic acid; iron / ethanol / 3 h / 60 - 70 °C 3: potassium iodide / toluene / 3 h / Reflux 4: triethylamine / toluene / 2 h / 15 - 25 °C View Scheme |
3-aminopiperidin-2-one
11-(chloroacetyl)-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: acetonitrile / 3 h / Heating 2: 28 percent / acetic acid / 11 h / Heating 3: 5percentPd on active carbon / pyridine / 17 h / Heating 4: 53 percent / triethylamine / dioxane / 8 h / Heating View Scheme |
isatoic anhydride
11-(chloroacetyl)-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: acetonitrile / 3 h / Heating 2: 28 percent / acetic acid / 11 h / Heating 3: 5percentPd on active carbon / pyridine / 17 h / Heating 4: 53 percent / triethylamine / dioxane / 8 h / Heating View Scheme |
2,3,4,4a,5,11-hexahydro-6H-pyrido<2,3-b><1,4>benzodiazepin-6-one
11-(chloroacetyl)-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 5percentPd on active carbon / pyridine / 17 h / Heating 2: 53 percent / triethylamine / dioxane / 8 h / Heating View Scheme |
3-(2'-aminobenzoyl)aminopiperidin-2-one
11-(chloroacetyl)-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 28 percent / acetic acid / 11 h / Heating 2: 5percentPd on active carbon / pyridine / 17 h / Heating 3: 53 percent / triethylamine / dioxane / 8 h / Heating View Scheme |
11-(chloroacetyl)-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one
6-benzylaminohexanoic acid {8-[(6-benzylaminohexanoyl)methylamino]octyl}methylamide
Conditions | Yield |
---|---|
With triethylamine; potassium iodide In N,N-dimethyl-formamide | 97% |
11-(chloroacetyl)-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one
11-{[4-(2-{2-[2-(2-{2-[2-(2-azido-ethoxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-ethoxy}-ethyl)-piperazin-1-yl]-acetyl}-5,11-dihydro-benzo[e]pyrido[3,2-b][1,4]diazepin-6-one
Conditions | Yield |
---|---|
With triethylamine In acetonitrile for 2h; Heating; | 96% |
11-(chloroacetyl)-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one
5-<(6-diethylamino)hexyloxy>-1,2,3,4-tetrahydroisoquinoline
Conditions | Yield |
---|---|
With sodium carbonate In acetonitrile for 5h; Heating; | 94% |
1-methyl-piperazine
11-(chloroacetyl)-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one
pirenzepine
Conditions | Yield |
---|---|
In benzene for 18h; Heating; Further byproducts given. Yields of byproduct given; | 87% |
4-[3-(piperidin-1-yl)propyl]piperidine
11-(chloroacetyl)-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one
Conditions | Yield |
---|---|
87% |
11-(chloroacetyl)-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one
N,N-diethyl-N'-benzyl-1,6-hexanediamine
N-<<(5,11-dihydro-6-oxo-6H-pyrido<2,3-b><1,4>-benzodiazepin-11-yl)carbonyl>methyl>-N-benzyl-N',N'-diethyl-1,6-hexanediamine
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide for 72h; Ambient temperature; | 86% |
11-(chloroacetyl)-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one
3-diethylaminomethyl-1,2,3,4-tetrahydroisoquinoline
Conditions | Yield |
---|---|
With sodium carbonate In acetonitrile for 5h; Heating; | 86% |
11-(chloroacetyl)-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one
5-<(4-diethylamino)butyloxy>-1,2,3,4-tetrahydroisoquinoline
Conditions | Yield |
---|---|
With sodium carbonate In acetonitrile for 5h; Heating; | 83% |
11-(chloroacetyl)-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one
11-[(4-{2-[2(2-Azidoethoxy)ethoxy]ethyl}piperazine-1-yl)acetyl]-5,11-dihydro-6H-pyrido-[2,3-b][1,4]benzodiazepine-6-one
Conditions | Yield |
---|---|
With potassium carbonate In acetonitrile for 20h; Heating; | 82% |
11-(chloroacetyl)-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one
Cycloheptyl-methyl-piperidin-2-ylmethyl-amine
11-(2-{2-[(Cycloheptyl-methyl-amino)-methyl]-piperidin-1-yl}-acetyl)-5,11-dihydro-benzo[e]pyrido[3,2-b][1,4]diazepin-6-one
Conditions | Yield |
---|---|
With sodium carbonate In acetonitrile for 5h; Heating; | 80% |
11-(chloroacetyl)-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one
2-<(N,N-Dipropylamino)methyl>piperidine
11-[2-(2-Dipropylaminomethyl-piperidin-1-yl)-acetyl]-5,11-dihydro-benzo[e]pyrido[3,2-b][1,4]diazepin-6-one
Conditions | Yield |
---|---|
With sodium carbonate In acetonitrile for 5h; Heating; | 76% |
1-(2-methyl-prop-2-en-1-yl)-piperazine
11-(chloroacetyl)-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one
11-{[4-(2-methyl-allyl)-piperazin-1-yl]-acetyl}-5,11-dihydro-benzo[e]pyrido[3,2-b][1,4]diazepin-6-one
Conditions | Yield |
---|---|
With sodium carbonate In ethanol; pyrographite | 75% |
11-(chloroacetyl)-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one
2-[3-(diethylamino)propyl]piperidine
11-[[2-[3-(Diethylamino)propyl]-1-piperidinyl]acetyl]-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one
Conditions | Yield |
---|---|
With sodium carbonate In acetonitrile for 5h; Heating; | 74% |
74% |
11-(chloroacetyl)-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one
5-<(7-diethylamino)heptyloxy>-1,2,3,4-tetrahydroisoquinoline
Conditions | Yield |
---|---|
With sodium carbonate In acetonitrile for 5h; Heating; | 73% |
11-(chloroacetyl)-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one
C57H74N10O4
C71H83N13O6
Conditions | Yield |
---|---|
With triethylamine; potassium iodide In N,N-dimethyl-formamide for 72h; Ambient temperature; | 70% |
11-(chloroacetyl)-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one
2-methyl-4-nitro-1H-imidazole
Conditions | Yield |
---|---|
With sodium hydride In methanol; N,N-dimethyl-formamide; paraffin 1.) 0 deg C, 30 min; 2.) rt, 18 h; | 70% |
11-(chloroacetyl)-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one
Tripitramine
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide for 18h; Ambient temperature; | 70% |
11-(chloroacetyl)-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one
N-<<(5,11-dihydro-6-oxo-6H-pyrido<2,3-b><1,4>-benzodiazepin-11-yl)carbonyl>methyl>-N',N'-diethyl-1,6-hexanediamine
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide for 12h; Ambient temperature; | 70% |
11-(chloroacetyl)-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one
5-<(5-diethylamino)pentyloxy>-1,2,3,4-tetrahydroisoquinoline
Conditions | Yield |
---|---|
With sodium carbonate In acetonitrile for 5h; Heating; | 70% |
1-(3-methyl-but-2-enyl)-piperazine
11-(chloroacetyl)-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one
Conditions | Yield |
---|---|
With hydrogenchloride; sodium carbonate In ethanol; isopropyl alcohol | 70% |
11-(chloroacetyl)-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one
Conditions | Yield |
---|---|
With sodium carbonate In acetonitrile | 68% |
11-(chloroacetyl)-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one
dimethyl amine
5,11-dihydro-11-<2-(dimethylamino)-1-oxoethyl>-6H-pyrido<2,3-b><1,4>benzodiazepin-6-one
Conditions | Yield |
---|---|
In acetone for 2h; Ambient temperature; | 67% |
11-(chloroacetyl)-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one
5-<(3-diethylamino)propoxy>-1,2,3,4-tetrahydroisoquinoline
Conditions | Yield |
---|---|
With sodium carbonate In acetonitrile for 5h; Heating; | 66% |
11-(chloroacetyl)-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one
Cyclohexyl-methyl-piperidin-2-ylmethyl-amine
11-(2-{2-[(Cyclohexyl-methyl-amino)-methyl]-piperidin-1-yl}-acetyl)-5,11-dihydro-benzo[e]pyrido[3,2-b][1,4]diazepin-6-one
Conditions | Yield |
---|---|
With sodium carbonate In acetonitrile for 5h; Heating; | 65% |
1H-imidazole
11-(chloroacetyl)-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one
5,11-dihydro-11-<(imidazo-1'-yl)-acetyl>-6H-pyrido<2,3-b><1,4>benzodiazepin-6-one
Conditions | Yield |
---|---|
In benzene for 1.5h; Heating; | 64.5% |
11-(chloroacetyl)-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one
5-<(2-diethylamino)ethoxy>-1,2,3,4-tetrahydroisoquinoline
Conditions | Yield |
---|---|
With sodium carbonate In acetonitrile for 5h; Heating; | 64% |
3-[3-[3-(diethylaminocarbonyl)-1-piperidinyl]-propyl]piperidine
11-(chloroacetyl)-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one
11-[[3-[3-[3-(Diethylaminocarbonyl)-1-piperidinyl]propyl]-1-piperidinyl]acetyl]-5,11-dihydro-6H-pyrido[2,3-b][1,4]-benzodiazepin-6-one
Conditions | Yield |
---|---|
In N-methyl-acetamide | 64% |
1-diethylaminomethyl-1,2,3,4-tetrahydroisoquinoline
11-(chloroacetyl)-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one
Conditions | Yield |
---|---|
With sodium carbonate In acetonitrile for 5h; Heating; | 63% |
propan-1-ol
11-(chloroacetyl)-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one
4-(2-(piperazin-1-yl)ethyl)morpholine
11-{[4-(2-morpholin-4-yl-ethyl)-piperazin-1-yl]-acetyl}-5,11-dihydro-benzo[e]pyrido[3,2-b][1,4]diazepin-6-one
Conditions | Yield |
---|---|
With sodium carbonate In ethanol | 63% |
Molecular Structure of 5,11-Dihydro-11-chloroacetyl-6H-pyrido[2,3-b][1,4]benzodiazepine-6-one (CAS NO.28797-48-0):
IUPAC Name: 11-(2-chloroacetyl)-5H-pyrido[2,3-b][1,4]benzodiazepin-6-one
Empirical Formula: C14H10ClN3O2
Molecular Weight: 287.7011
H bond acceptors: 5
H bond donors: 1
Freely Rotating Bonds: 1
Polar Surface Area: 53.51 Å2
Index of Refraction: 1.637
Molar Refractivity: 72.98 cm3
Molar Volume: 203.2 cm3
Surface Tension: 59.2 dyne/cm
Density: 1.415 g/cm3
Flash Point: 244.7 °C
Enthalpy of Vaporization: 74.57 kJ/mol
Boiling Point: 481.1 °C at 760 mmHg
Vapour Pressure: 2.06E-09 mmHg at 25°C
InChI
InChI=1/C14H10ClN3O2/c15-8-12(19)18-11-6-2-1-4-9(11)14(20)17-10-5-3-7-16-13(10)18/h1-7H,8H2,(H,17,20)
Smiles
N1(c2c(C(=O)Nc3c1nccc3)cccc2)C(=O)CCl
5,11-Dihydro-11-chloroacetyl-6H-pyrido[2,3-b][1,4]benzodiazepine-6-one , with CAS number of 28797-48-0, can be called 11-(Chloroacetyl)-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one ; 6H-pyrido[2,3-b][1,4]benzodiazepin-6-one, 11-(2-chloroacetyl)-5,11-dihydro- ; 6H-Pyrido[2,3-b][1,4]benzodiazepin-6-one, 11-(chloroacetyl)-5,11-dihydro- ; (6H)Pyrido[2,3-b][1,4]benzodiazepin-6-one, 5-hydro-11-(monochloromethyl)carbonyl- ; 11-(Chloroacetyl)-5,11-dihydro-6H-pyrido(2,3-b)(1,4)benzodiazepin-6-one .
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