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Product Details of [ 22245-92-7 ]

CAS No. :22245-92-7 MDL No. :MFCD09260841
Formula : C10H12N2O Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 176.22 Pubchem ID :-
Synonyms :

Safety of [ 22245-92-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 22245-92-7 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 22245-92-7 ]

[ 22245-92-7 ] Synthesis Path-Downstream   1~50

  • 1
  • [ 22246-45-3 ]
  • [ 22245-92-7 ]
YieldReaction ConditionsOperation in experiment
96% With hydrazine hydrate monohydrate In ethanol for 0.5h; Heating;
93.6% With palladium on activated charcoal; hydrogen In tetrahydrofuran; methanol at 20℃; for 16h; 18.2 Step 2: 7-amino-1,3,4,5-tetrahydro-2H-benzo[b]azepin-2-one A solution of 7-nitro-1,3,4,5-tetrahydro-2H-benzo [b] azepan-2-one (2.5 g, 12.1 mmol) in methanol / tetrahydrofuran / 1, v / v)Add dry palladium on carbon (250 mg).Hydrogen at room temperature for 16h,The filtrate was concentrated to give 7-amino-1,3,4,5-tetrahydro-2H-benzo [b] azepin-2-one (2.0 g) in a yield of 93.6%.
78% With palladium on activated charcoal; hydrogen In tetrahydrofuran; methanol at 20℃; 8.4 Step 4:7-amino-1,3,4,5-tetrahydro-2H-benzo [b] azepan-2-one At room temperature,7-nitro-1,3,4,5-tetrahydro-2H-benzene [b] azepin-2-one(1.60 g, 10 mmol) was dissolved in tetrahydrofuran (60 mL) and methanol (20 mL)Palladium carbon (0.16 g) was added and stirred at room temperature overnight under a hydrogen atmosphere.After the reaction is filtered,Washed with ethyl acetate,The solvent was dried under reduced pressure to give 7-amino-1,3,4,5-tetrahydro-2H-benzo [b] azepine-2-one (1.0 g) in 78% yield.
76% With ammsnium formate In tetrahydrofuran; methanol at 20℃; for 2h; 8.3 To a solution OF 7-NITRO-1, 3,4, 5-tetrahydro-benzo [b] AZEPIN-2-ONE (0.20 g, 0.97 mmol) in a mixture of tetrahydrofuran and methanol (8 ML/2 mL), ammonium formate (0.245 g, 3. 88 mmol) was added, followed by 10 % palladium on carbon. The mixture was stirred at room temperature for 2 hours and filtered through celite. The filtrate was concentrated under vacuum, treated with water and extracted with ethyl acetate. The organic extracts were washed with brine and dried OVER NA2S04 to give the title compound. Yield 0.13 g (76 %). 1H NMR (400 MHz, CDC13) 8 7.38 (br s, 1H), 6.80 (d, 1H), 6.56 (m, 2H), 3.62 (br s, 2H), 2.70 (t, 2H), 2.38 (m, 2H), 2.20 (t, 2H).
With reducing agent
With 10% palladium on activated carbon; hydrazine hydrate monohydrate In ethanol at 60℃;
1.2 Step 2: Step 2: 7-amino-1,3,4,5-tetrahydro-2H-1-benzazepine-2-one (Compound 3) Palladium on carbon(1.5 g, 0.014 mol) was added to a solution of compound 2 (5.0 g, 0.024 mol) in ethanol (100 mL), and the mixture was stirred at room temperature overnight under the protection of hydrogen. The palladium on carbon was removed by filtration, and the solvent was removed by concentration, the residue was purified by column chromatography to obtain a compound 3 (2.5 g, yield: 59%). MS (ESI): Calcd. for C10H12N2O 176; Found 177 [M+H]+.
With palladium on activated charcoal; hydrogen In ethanol at 20℃; 1.2 Step 2:7-amino-1,3,4,5-tetrahydro-2H-1-benzazepine-2-one (Compound 3) Palladium on carbon(1.5 g, 0.014 mol) was added to a solution of compound 2 (5.0 g, 0.024 mol) in ethanol (100 mL), and the mixture was stirred at room temperature overnight under the protection of hydrogen. The palladium on carbon was removed by filtration, and the solvent was removed by concentration, the residue was purified by column chromatography to obtain a compound 3 (2.5 g, yield: 59%). MS (ESI): Calcd. for C10H12N2O 176; Found 177 [M+H]+.
With palladium on activated charcoal; hydrogen In ethanol at 20℃; 1.2 Step 2:7-amino-1,3,4,5-tetrahydro-2H-1-benzazepine-2-one (Compound 3) Palladium on carbon(1.5 g, 0.014 mol) was added to a solution of compound 2 (5.0 g, 0.024 mol) in ethanol (100 mL), and the mixture was stirred at room temperature overnight under the protection of hydrogen. The palladium on carbon was removed by filtration, and the solvent was removed by concentration, the residue was purified by column chromatography to obtain a compound 3 (2.5 g, yield: 59%). MS (ESI): Calcd. for C10H12N2O 176; Found 177 [M+H]+.

  • 2
  • [ 4424-80-0 ]
  • [ 22245-92-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 60 percent / HNO3,H2SO4 2: 96 percent / 95percent N2H4*H2O / 4percentPd,C / ethanol / 0.5 h / Heating
Multi-step reaction with 2 steps 1: agent for nitration 2: reducing agent
Multi-step reaction with 2 steps 1: sulfuric acid; HNO3 / 0.25 h / 0 °C 2: 10% palladium on activated carbon; hydrazine hydrate monohydrate / ethanol / 60 °C
Multi-step reaction with 2 steps 1: sulfuric acid; HNO3 / 0.5 h / 0 °C 2: palladium on activated charcoal; hydrogen / tetrahydrofuran; methanol / 20 °C
Multi-step reaction with 2 steps 1: sulfuric acid; HNO3 / 0.17 h / Cooling with ice 2: hydrogen; palladium on activated charcoal / tetrahydrofuran; methanol / 16 h / 20 °C
Multi-step reaction with 2 steps 1: sulfuric acid
Multi-step reaction with 2 steps 1: HNO3; sulfuric acid / 0.33 h / 0 °C 2: hydrogen; palladium on activated charcoal / ethanol / 20 °C

  • 3
  • 1-tetralone oxime [ No CAS ]
  • [ 22245-92-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: polyphosphoric acid 2: 60 percent / HNO3,H2SO4 3: 96 percent / 95percent N2H4*H2O / 4percentPd,C / ethanol / 0.5 h / Heating
  • 4
  • [ 22245-92-7 ]
  • [ 165127-55-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 1.) aq. HCl, NaNO2 / 1.) from 0 to 5 deg C, 2.) H2O, from 0 to 5 deg C 2: ethyl acetate / 0.5 h / 55 °C 3: 80 percent / KOH / ethanol / 2 h / Heating
  • 5
  • [ 22245-92-7 ]
  • 2,3,4,5-tetrahydro-1H-1-benzazepin-2-one-7-mercaptoacetic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 1.) aq. HCl, NaNO2 / 1.) from 0 to 5 deg C, 2.) H2O, from 0 to 5 deg C 2: ethyl acetate / 0.5 h / 55 °C 3: 80 percent / KOH / ethanol / 2 h / Heating 4: 91 percent / aq. KOH / 0.17 h / 20 - 95 °C
  • 6
  • [ 22245-92-7 ]
  • [ 165127-54-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 1.) aq. HCl, NaNO2 / 1.) from 0 to 5 deg C, 2.) H2O, from 0 to 5 deg C 2: ethyl acetate / 0.5 h / 55 °C
  • 7
  • [ 22245-92-7 ]
  • bis-2,3,4,5-tetrahydro-1H-1-benzazepin-2-one-7-disulphide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 1.) aq. HCl, NaNO2 / 1.) from 0 to 5 deg C, 2.) H2O, from 0 to 5 deg C 2: ethyl acetate / 0.5 h / 55 °C 3: 80 percent / KOH / ethanol / 2 h / Heating 4: 74 percent / 36,6percent H2O2 / ethanol / 40 °C
  • 8
  • [ 529-34-0 ]
  • [ 22245-92-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 2: polyphosphoric acid 3: 60 percent / HNO3,H2SO4 4: 96 percent / 95percent N2H4*H2O / 4percentPd,C / ethanol / 0.5 h / Heating
  • 9
  • [ 22245-92-7 ]
  • [ 104479-37-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: acetic acid 2: 10 g / fuming HNO3, conc. H2SO4 3: 4 g / conc. HCl / 3 h / Heating 4: 1.0 g / 1,2-dichloro-benzene / 16 h / Heating 5: H2 / 10percent Pd/C
  • 10
  • [ 22245-92-7 ]
  • [ 104479-36-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: acetic acid 2: 10 g / fuming HNO3, conc. H2SO4 3: 4 g / conc. HCl / 3 h / Heating 4: 1.0 g / 1,2-dichloro-benzene / 16 h / Heating
  • 11
  • [ 22245-92-7 ]
  • [ 104479-35-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: acetic acid 2: 10 g / fuming HNO3, conc. H2SO4 3: 4 g / conc. HCl / 3 h / Heating
  • 12
  • [ 22245-92-7 ]
  • [ 104479-34-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: acetic acid 2: 10 g / fuming HNO3, conc. H2SO4
  • 13
  • [ 22245-92-7 ]
  • methyl 6-oxo-1,5,6,7,8,9-hexahydroimidazo<4,5-h><1>benzazepin-2-ylcarbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: acetic acid 2: 10 g / fuming HNO3, conc. H2SO4 3: 4 g / conc. HCl / 3 h / Heating 4: 1.0 g / 1,2-dichloro-benzene / 16 h / Heating 5: H2 / 10percent Pd/C 6: 0.6 g / p-TsOH / methanol / 3 h / Heating
Multi-step reaction with 2 steps 1: p-TsOH / methanol / 3 h / Heating 2: 1.) Pb(OAc)4, 2.) MeOH / 1.) CHCl3, reflux, 1 h, 2.) reflux, 1 h
  • 14
  • [ 22245-92-7 ]
  • (7-Oxo-3,6,7,8,9,10-hexahydro-1,3,6-triaza-cyclohepta[e]inden-2-yl)-carbamic acid methyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: p-TsOH / methanol / 3 h / Heating 2: 1.) Pb(OAc)4, 2.) MeOH / 1.) CHCl3, reflux, 1 h, 2.) reflux, 1 h
  • 15
  • [ 22245-92-7 ]
  • 7-Brom-1,3,4,5-tetrahydro-2H-benz<b>azepin-2-on-phenylhydrazon-hydrochlorid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 2: P2S5, sea sand / Heating 3: 1.) NaH / 1.) DMF, toluene, 2.) DMF, toluene, overnight 4: 34 percent / ethanol / Heating
  • 16
  • [ 22245-92-7 ]
  • 7-Chlor-1,3,4,5-tetrahydro-2H-benz<b>azepin-2-on-phenylhydrazon-hydrochlorid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 2: P2S5, sea sand / Heating 3: 1.) NaH / 1.) DMF, toluene, 2.) DMF, toluene, overnight 4: 23 percent / ethanol / Heating
  • 17
  • [ 22245-92-7 ]
  • [ 60456-26-0 ]
  • [ 741254-42-2 ]
YieldReaction ConditionsOperation in experiment
75% With lithium perchlorate; In acetonitrile; at 20℃; for 16h; To a stirred solution OF 7-AMINO-1, 3,4, 5-tetrahydro-benzo [b] azepin-2-one (0.90 g, 5.1 mmol) and (R) -glycidyl butyrate (0.74 g, 5.1 mmol) in anhydrous acetonitrile (45 mL), lithium perchlorate (0.70 g, 6.6 mmol) was added, and the mixture was stirred at room temperature for several hours. The solvent was removed under vacuum and the residue was partitioned between water and ethyl acetate. The organic layer was separated, washed with water, saturated NaHCO3 and brine, dried over NA2S04 and concentrated under vacuum. Purification by column chromatography on silica gel (ethyl acetate/methanol 19: 1) gave (R)- Butyric acid 2-hydroxy-3-(2-oxo-2, 3,4, 5-TETRAHYDRO-LH-BENZO [b] azepin-7- ylamino) -propyl ester. Yield 1.2 g (75 %). H NMR (400 MHz, CDC13) 8 8.24 (s, 1H), 6.78 (d, 1H), 6.48 (m, 2H), 4.30 (br s, 1H), 4.20 (m, 2H), 4.10 (m, 1H), 3.92 (br s, 1H), 3.28 (m, 1H), 3.12 (m, 1H), 2.63 (t, 2H), 2.31 (t, 2H), 2.28 (m, 2H), 2.11 (m, 2H), 1.67 (m, 2H), 0.92 (t, 3H). MS: m/z 320 (M+).
  • 19
  • [ 939043-29-5 ]
  • [ 22246-68-0 ]
  • [ 22245-92-7 ]
YieldReaction ConditionsOperation in experiment
Stage #1: (1E)-6-Amino-3,4-dihydro-1(2H)-naphthalenone oxime at 90 - 120℃; for 4.5h; Stage #2: With water at 0℃; for 0.5h; Stage #3: With sodium hydroxide In water at 90℃; Intermediate 2; 7-Amino-2,3,4,5-tetrahydro-1H-2-benzazepin-1-one; Polyphosphoric acid (488 g) was heated to 90° C. in a 2 litre flask equipped with a mechanical stirrer. (1E)-6-Amino-3,4-dihydro-1(2H)-naphthalenone oxime (see Intermediate 1) (34.6 g, 0.196 mol) was added in portions over 1 h with rapid stirring. The temperature was increased to 110° C. and the mixture was heated for 1.5 h. As a fine solid suspension was still present, the mixture was heated at 120° C. for a further 2 h and then poured onto iced water (1500 ml). The gum was broken up and stirred for 30 min and then basified by the careful addition of 10M aqueous sodium hydroxide solution (1300 ml) keeping the temperature below 90° C. 10 g of solid sodium hydroxide was added and the mixture was cooled in an ice bath and a solid precipitated. Around one third of the mixture was filtered through a sinter funnel. The solid was re-suspended in a mixture of DCM and water and re-filtered. This was repeated until a total of 4000 ml (1:1) DCM:water had been used. The remaining two thirds of material was poured onto a much larger sinter funnel and a similar extraction and filtration method was used once more collecting a further 4000 ml of 1:1 DCM:water. The mixture was left to stand for 16 h. Since some solid had filtered through, the mixtures were refiltered. This mixture was filtered (×3) as more solid continued to precipitate. The layers were separated and the aqueous was washed with DCM (1000 ml). The organic extracts were combined and evaporated to give the title compound as a brown solid (27 g, contains 4% 7-amino-1,3,4,5-tetrahydro-2H-1-benzazepin-2-one).Mass spectrum: Found: MH+ 177H.p.l.c. Rt 1.51 min
  • 20
  • [ 959246-74-3 ]
  • [ 22245-92-7 ]
  • [ 1022946-74-2 ]
YieldReaction ConditionsOperation in experiment
32% With hydrogenchloride In 1,4-dioxane; isopropyl alcohol at 130℃; for 0.333333h; Microwave irradiation; 2-[5-Chloro-2-(2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-8-ylamino)-pyrimidin-4-ylamino]-3-fluoro-N-methyl-benzamide (24) 2-(2,5-Dichloro-pyrimidin-4-ylamino)-3-fluoro-N-methyl-benzamide and 2-(2,5-Dichloro-pyrimidin-4-ylamino)-3-fluoro-N-methyl-benzamide (3b) (1.1 eq) were dissolved in isopropyl alcohol (3 mL). 4.0 M HCl in dioxane (1.1 eq) was added and the reaction was heated at 130 °C in a microwave for 20 minutes. The reaction was then concentrated under reduced pressure and the residue was taken up in dichloromethane (20 mL) and washed with sat. NaHCO3 (20 mL). The organic layer was dried (sodium sulfate), filtered, and concentrated under reduced pressure. The residue was purified by chromatography to obtain the product as a yellow solid (32%). mp 180-190 °C; LCMS: m/z = 455 (M+H+); 1H NMR (400 MHz, DMSO-d6) δ 9.35-9.22 (m, 3H), 8.56-8.47 (m, 1H), 8.17 (s, 1H), 7.50-7.42 (m, 2H), 7.40-7.31 (m, 1H), 7.23 (d, 1H, J = 8.3 Hz) 7.09 (s, 1H), 6.93 (d, 1H, J = 8.3 Hz), 2.72 (d, 3H, J = 4.4 Hz), 2.56 (t, 2H, J = 6.2 Hz), 2.12-1.97 (m, 4H).
  • 21
  • [ 22245-92-7 ]
  • 5-(2,4-dihydroxy-5-isopropylphenyl)-N-ethyl-4-(2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepine-7-yl)-4H-1,2,4-triazole-3-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N,N-dimethyl-formamide / 1 h / 20 °C 2: mercury dichloride; pyridine / 1,4-dioxane / 80 °C / Microwave irradiation
  • 22
  • [ 22245-92-7 ]
  • 7-(3-(2,4-dihydroxy-5-isopropylphenyl)-4H-1,2,4-triazol-4-yl)-2,3,4,5-tetrahydro-1H-benzazepin-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: N,N-dimethyl-formamide / 1 h / 20 °C 2: hydrazine hydrate / 1,4-dioxane / 2 h / Reflux 3: tetrahydrofuran / -78 - 20 °C / Inert atmosphere 4: potassium carbonate / ethanol / 15 h / 80 °C
  • 23
  • [ 22245-92-7 ]
  • ethyl 5-(2,4-dihydroxy-5-isopropylphenyl)-4-(2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-7-yl)-4H-1,2,4-triazole-3-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: N,N-dimethyl-formamide / 1 h / 20 °C 2: hydrazine hydrate / 1,4-dioxane / 2 h / Reflux 3: tetrahydrofuran / -78 - 20 °C / Inert atmosphere
  • 24
  • [ 22245-92-7 ]
  • 5-(2,4-dihydroxy-5-isopropylphenyl)-N-methoxy-4-(2-oxo-2,3,4,5-tetrahydro-Benzo [b] azepin-7-yl)-4H-1,2,4-triazole-3-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N,N-dimethyl-formamide / 1 h / 20 °C 2: mercury dichloride; pyridine / 1,4-dioxane / 0.33 h / 80 °C / Microwave irradiation
  • 25
  • [ 22245-92-7 ]
  • (E)-2,4-dihydroxy-5-isopropyl-N-(2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-7-yl)benzohydrazonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N,N-dimethyl-formamide / 1 h / 20 °C 2: hydrazine hydrate / 1,4-dioxane / 2 h / Reflux
  • 26
  • [ 22245-92-7 ]
  • 5-(2,4-dihydroxy-5-isopropylphenyl)-4-(2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-7-yl)-4H-1,2,4-triazole-3-hydrazide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: N,N-dimethyl-formamide / 1 h / 20 °C 2: hydrazine hydrate / 1,4-dioxane / 2 h / Reflux 3: tetrahydrofuran / -78 - 20 °C / Inert atmosphere 4: hydrazine hydrate / ethanol / 2 h / 80 °C
  • 27
  • [ 22245-92-7 ]
  • N'-(tert-butyl)-5-(2,4-dihydroxy-5-isopropylphenyl)-4-(2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-7-yl)-4H-1,2,4-triazole-3-hydrazide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: N,N-dimethyl-formamide / 1 h / 20 °C 2: hydrazine hydrate / 1,4-dioxane / 2 h / Reflux 3: acetic acid / ethanol / 15 h / 80 °C
  • 28
  • [ 1046490-82-7 ]
  • [ 22245-92-7 ]
  • 2,4-dihydroxy-5-isopropyl-N-(2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-7-yl)benzothiamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% In N,N-dimethyl-formamide at 20℃; for 1h; 8.7 Step 7: 2,4-dihydroxy-5-isopropyl-N-(2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-7-yl)benzothiamide At room temperature,A solution of bis ((2,4-dihydroxy-5-isopropylphenyl) methanethione) (1.8 g, 4.11 mmol) was dissolved in N, N-dimethylformamide (25 mL)The 7-amino-1,3,4,5-tetrahydro-2H-benzo [b] azepan-2-one (1.45 g, 8.22 mmol) was then added to the reaction system,Stir at room temperature for one hour.The reaction system was diluted with ethyl acetate (50 mL)Then washed with brine,The organic phase was dried over anhydrous sodium sulfate,filter,Spin dry.The crude product was purified by column chromatography (petroleum ether / ethyl acetate (V / V): 1/1 --- dichloromethane / methanol (V / V): 25/1)2,4-dihydroxy-5-isopropyl-N- (2-oxo-2,3,4,5-tetrahydro-1H-benzo [b] azepine-7-yl) The amide (1.30 g) was obtained in 70% yield.
  • 29
  • [ 22245-92-7 ]
  • 7-amino-1,3,4,5-tetrahydro-2H-benzo[b]azepin-2-thione [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tetraphosphorus decasulfide; triethylamine In acetonitrile at 90℃; for 16h; Cooling with ice; 18.3 Step 3: 7-amino-1,3,4,5-tetrahydro-2H-benzo[b]azepin-2-thione Triethylamine (6 mL, 42.3 mmol) was dissolved in acetonitrile (100 mL)To the ice bath was added phosphorus pentasulfide (2.84 g, 12.8 mmol)After stirring for 5 min, 7-amino-1,3,4,5-tetrahydro-2H-benzo [b] azepan-2-one (1.5 g, 8.5 mmol) was added.The reaction solution was heated to 90 ° C for 16 h.Concentrated, diluted with dichloromethane, washed with saturated brine, dried and concentrated to give 7-amino-1,3,4,5-tetrahydro-2H-benzo [b] azepine-2-thione (1.3 g ), The yield was 79.4%.
  • 30
  • [ 22245-92-7 ]
  • (Z)-2-hydrazono-2,3,4,5-tetrahydro-1H-benzo[b]azepin-7-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: tetraphosphorus decasulfide; triethylamine / acetonitrile / 16 h / 90 °C / Cooling with ice 2: hydrazine hydrate / tetrahydrofuran / 2 h / 80 °C
  • 31
  • [ 22245-92-7 ]
  • (Z)-2-(((E)-5-isopropyl-2,4-dimethoxybenzylidene)hydrazono)-2,3,4,5-tetrahydro-1H-benzo[b]azepin-7-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: tetraphosphorus decasulfide; triethylamine / acetonitrile / 16 h / 90 °C / Cooling with ice 2: hydrazine hydrate / tetrahydrofuran / 2 h / 80 °C 3: ethanol / 1 h / 80 °C
  • 32
  • [ 22245-92-7 ]
  • 1-(5-isopropyl-2,4-dimethoxyphenyl)-5,6-dihydro-4H-benzo[f][1,2,4]triazolo[4,3-a]azepin-8-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: tetraphosphorus decasulfide; triethylamine / acetonitrile / 16 h / 90 °C / Cooling with ice 2: hydrazine hydrate / tetrahydrofuran / 2 h / 80 °C 3: ethanol / 1 h / 80 °C 4: iron(III) chloride / ethanol / 6 h / 80 °C
  • 33
  • [ 22245-92-7 ]
  • 2-chloro-N-(2-(5-isopropyl-2,4-dimethoxyphenyl)-5,6-dihydro-4H-benzo[f][1,2,4]triazolo[1,5-a]azepin-8-yl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: tetraphosphorus decasulfide; triethylamine / acetonitrile / 16 h / 90 °C / Cooling with ice 2: hydrazine hydrate / tetrahydrofuran / 2 h / 80 °C 3: ethanol / 1 h / 80 °C 4: iron(III) chloride / ethanol / 6 h / 80 °C 5: triethylamine / dichloromethane / 2 h / 20 °C
  • 34
  • [ 22245-92-7 ]
  • N-(2-(5-isopropyl-2,4-dimethoxyphenyl)-5,6-dihydro-4H-benzo[f][1,2,4]triazolo[1,5-a]azepin-8-yl)-2-morpholinoacetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: tetraphosphorus decasulfide; triethylamine / acetonitrile / 16 h / 90 °C / Cooling with ice 2: hydrazine hydrate / tetrahydrofuran / 2 h / 80 °C 3: ethanol / 1 h / 80 °C 4: iron(III) chloride / ethanol / 6 h / 80 °C 5: triethylamine / dichloromethane / 2 h / 20 °C 6: caesium carbonate / N,N-dimethyl-formamide / 16 h / 20 °C
  • 35
  • [ 22245-92-7 ]
  • N-(2-(2,4-dihydroxy-5-isopropylphenyl)-5,6-dihydro-4H-benzo[f][1,2,4]triazolo[1,5-a]azepine-8-yl)-2-morpholinoacetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: tetraphosphorus decasulfide; triethylamine / acetonitrile / 16 h / 90 °C / Cooling with ice 2: hydrazine hydrate / tetrahydrofuran / 2 h / 80 °C 3: ethanol / 1 h / 80 °C 4: iron(III) chloride / ethanol / 6 h / 80 °C 5: triethylamine / dichloromethane / 2 h / 20 °C 6: caesium carbonate / N,N-dimethyl-formamide / 16 h / 20 °C 7: boron tribromide / dichloromethane / 16 h / 20 °C / Cooling with ice
  • 36
  • [ 22245-92-7 ]
  • 4-(8-amino-5,6-dihydro-4H-benzo[f][1,2,4]triazolo[1,5-a]azepin-2-yl)-6-isopropylbenzene-1,3-diol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: tetraphosphorus decasulfide; triethylamine / acetonitrile / 16 h / 90 °C / Cooling with ice 2: hydrazine hydrate / tetrahydrofuran / 2 h / 80 °C 3: ethanol / 1 h / 80 °C 4: iron(III) chloride / ethanol / 6 h / 80 °C 5: boron tribromide / dichloromethane / 16 h / 20 °C / Cooling with ice
  • 37
  • 8-cyclobutyl-2-(methylsulfinyl)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidine-6-carbonitrile [ No CAS ]
  • [ 22245-92-7 ]
  • 8-cyclopentyl-7-oxo-2-((2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-7-yl)amino)-7,8-dihydropyrido[2,3-d]pyrimidine-6-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
In toluene at 100℃; for 2h; S41 Synthesis of 8-cyclopentyl-7-oxo-2-((2-oxo-2,3,4,5-tetrahydro-1H- benzo[b]azepin-7-yl)amino)-7,8-dihydropyrido[2,3-d]pyrimidine-6-carbonitrile (Compound no. 83) To a stirred solution of 8-cyclobutyl-2-(methylsulfinyl)-7-oxo-7,8-dihydropyrido[2,3- d]pyrimidine-6-carbonitrile (100 mg, 0.33 mmol, 1 equiv) in toluene (5 mL), was added 7- amino-1,3,4,5-tetrahydro-2H-benzo[b]azepin-2-one (64 mg, 0.69 mmol, 1.1 equiv). The resultant reaction mixture was allowed to stir at 100 °C for 2h. Progress of the reaction was monitored by LCMS. After completion of the reaction, solid observed were filtered and dried under vacuum to obtain crude compound, which was purified by recrystallization with methanol to obtain desired product. LCMS: 415 [M+H] +; 1H NMR: (400 MHz, DMSO-d6): d 10.55 (br. s., 1H), 9.48 (br. s., 1H), 8.83 (br. s., 1H), 8.57 (br. s., 1H), 7.71 (br. s., 1H), 7.42 (br. s., 1H), 7.18 (br. s., 1H), 6.96 (d, J = 8.3 Hz, 1H), 5.81 (br. s., 1H), 2.67 (br. s., 2H), 2.16 (br. s., 6H), 1.89 (br. s., 2H), 1.80 (br. s., 2H), 1.56 (br. s., 2H)
  • 38
  • N-(4-((2-chloropyrimidin-4-yl)oxy)phenyl)-N'-(4-fluorophenyl)cyclopropane-1,1-dicarboxamide [ No CAS ]
  • [ 22245-92-7 ]
  • N-(4-fluorophenyl)-N-(4-((2-((2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-7-yl)amino)pyrimidin-4-yl)oxy)phenyl)cyclopropane-1,1-dicarboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
64.5% With toluene-4-sulfonic acid In N,N-dimethyl-formamide at 90℃; for 10h; 5.4 General procedure for preparation of compound 15 General procedure: To a solution of the intermediate 14 (11.0mmol) and R2-substituedaniline (10.0mmol) in DMF (20mL) was added p-Toluenesulfonic acid monohydrate (7.60g, 40.0mmol). The mixture was stirred at 90°C for 10h. Then water (50mL) was added to precipitate white solid, which was filtered off, and recrystallized from ethanol to afford 15.
  • 39
  • [ 1584220-26-7 ]
  • [ 22245-92-7 ]
  • N-(3-fluoro-4-((2-((2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-7-yl)amino)pyrimidin-4-yl)oxy)phenyl)-N-(4-fluorophenyl)cyclopropane-1,1-dicarboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
70.2% With toluene-4-sulfonic acid In N,N-dimethyl-formamide at 90℃; for 10h; 5.4 General procedure for preparation of compound 15 General procedure: To a solution of the intermediate 14 (11.0mmol) and R2-substituedaniline (10.0mmol) in DMF (20mL) was added p-Toluenesulfonic acid monohydrate (7.60g, 40.0mmol). The mixture was stirred at 90°C for 10h. Then water (50mL) was added to precipitate white solid, which was filtered off, and recrystallized from ethanol to afford 15.
  • 40
  • [ 1022954-85-3 ]
  • [ 22246-68-0 ]
  • [ 22245-92-7 ]
YieldReaction ConditionsOperation in experiment
at 120℃; for 2h; Inert atmosphere; 5.2 Step 2) 7-amino-2,3,4,5-tetrahydro-2-benzazepin-1-one (3) and 7-amino-1,3,4,5-tetrahydro- 1-benzazepin-2-one A mixture of 6-aminotetralin-1-one oxime (880 mg, 4.99 mmol) in PPA (10 mL) was stirred at 120 °C for 2 h. The mixture was cooled to 90 °C, then poured into ice. Then the mixture was neutralized with 4N NaOH aq. (~20 mL) to pH=8, and extracted with EtOAc (100 mL X 2). The EtOAc layer was washed with brine (30 mL), dried over Na2SO4 and concentrated under reduced pressure to give a mixture of 7-amino-2,3,4,5-tetrahydro-2-benzazepin-1-one (3) and 7-amino- 1,3,4,5-tetrahydro-1-benzazepin-2-one (850 mg) as brown solids ESI MS [M+H]+: 177.1
at 120℃; for 2h; Inert atmosphere; 5.2 Step 2) 7-amino-2,3,4,5-tetrahydro-2-benzazepin-1-one (3) and 7-amino-1,3,4,5-tetrahydro- 1-benzazepin-2-one A mixture of 6-aminotetralin-1-one oxime (880 mg, 4.99 mmol) in PPA (10 mL) was stirred at 120 °C for 2 h. The mixture was cooled to 90 °C, then poured into ice. Then the mixture was neutralized with 4N NaOH aq. (~20 mL) to pH=8, and extracted with EtOAc (100 mL X 2). The EtOAc layer was washed with brine (30 mL), dried over Na2SO4 and concentrated under reduced pressure to give a mixture of 7-amino-2,3,4,5-tetrahydro-2-benzazepin-1-one (3) and 7-amino- 1,3,4,5-tetrahydro-1-benzazepin-2-one (850 mg) as brown solids ESI MS [M+H]+: 177.1
  • 41
  • 8-chloro-3-(3-fluoro-4-methoxyphenyl)imidazo[1,2-a]pyrazine [ No CAS ]
  • [ 22246-68-0 ]
  • [ 22245-92-7 ]
  • 7-[[3-(3-fluoro-4-methoxy-phenyl)imidazo[1,2-a]pyrazin-8-yl]amino]-1,3,4,5-tetrahydro-1-benzazepin-2-one hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
8.1 mg Stage #1: 8-chloro-3-(3-fluoro-4-methoxyphenyl)imidazo[1,2-a]pyrazine; 7-amino-2,3,4,5-tetrahydro-2-benzazepin-1-one; 7-Amino-1,3,4,5-tetrahydro-2H-benz<b>azepin-2-on With glacial acetic acid In acetonitrile at 90℃; for 16h; Inert atmosphere; Stage #2: With hydrogenchloride Inert atmosphere; 5.3 Step 3) 7-[[3-(3-fluoro-4-methoxy-phenyl)imidazo[1,2-a]pyrazin-8-yl]amino]-1,3,4,5- tetrahydro-1-benzazepin-2-one hydrochloride A mixture of 8-chloro-3-(3-fluoro-4-methoxy-phenyl)imidazo[1,2-a]pyrazine (150 mg, 0.540 mmol), a mixture of 7-amino-2,3,4,5-tetrahydro-2-benzazepin-1-one and 7-amino-1,3,4,5- tetrahydro-1-benzazepin-2-one (105 mg, 0.6 mmol) in ACN (1.8 mL) and acetic acid (0.200 mL) was stirred at 90 °C for 16 h. The mixture was concentrated under reduced pressure. The residue was purified by prep-TLC (DCM:MeOH=10:1) to give a crude product, which was further purified by prep-HPLC (HCl as additive) to give the title compound (8.1 mg) as a yellow solid. ESI MS [M+H]+: 418.1 1H NMR (400 MHz, DMSO-d6) δ ppm 10.57 (br s, 1 H) 8.14 (s, 1 H) 8.07 (d, J=4.77 Hz, 1 H) 7.99 (br d, J=6.53 Hz, 2 H) 7.91 (s, 1 H) 7.59 - 7.67 (m, 2 H) 7.48 - 7.57 (m, 2 H) 7.36 - 7.45 (m, 1 H) 3.94 (s, 3 H) 2.97 (br d, J=5.77 Hz, 2 H) 2.76 (br t, J=6.90 Hz, 2 H) 1.93 (br t, J=6.65 Hz, 2 H).
8.1 mg Stage #1: 8-chloro-3-(3-fluoro-4-methoxyphenyl)imidazo[1,2-a]pyrazine; 7-amino-2,3,4,5-tetrahydro-2-benzazepin-1-one; 7-Amino-1,3,4,5-tetrahydro-2H-benz<b>azepin-2-on With glacial acetic acid In acetonitrile at 90℃; for 16h; Inert atmosphere; Stage #2: With hydrogenchloride Inert atmosphere; 5.3 Step 3) 7-[[3-(3-fluoro-4-methoxy-phenyl)imidazo[1,2-a]pyrazin-8-yl]amino]-1,3,4,5- tetrahydro-1-benzazepin-2-one hydrochloride A mixture of 8-chloro-3-(3-fluoro-4-methoxy-phenyl)imidazo[1,2-a]pyrazine (150 mg, 0.540 mmol), a mixture of 7-amino-2,3,4,5-tetrahydro-2-benzazepin-1-one and 7-amino-1,3,4,5- tetrahydro-1-benzazepin-2-one (105 mg, 0.6 mmol) in ACN (1.8 mL) and acetic acid (0.200 mL) was stirred at 90 °C for 16 h. The mixture was concentrated under reduced pressure. The residue was purified by prep-TLC (DCM:MeOH=10:1) to give a crude product, which was further purified by prep-HPLC (HCl as additive) to give the title compound (8.1 mg) as a yellow solid. ESI MS [M+H]+: 418.1 1H NMR (400 MHz, DMSO-d6) δ ppm 10.57 (br s, 1 H) 8.14 (s, 1 H) 8.07 (d, J=4.77 Hz, 1 H) 7.99 (br d, J=6.53 Hz, 2 H) 7.91 (s, 1 H) 7.59 - 7.67 (m, 2 H) 7.48 - 7.57 (m, 2 H) 7.36 - 7.45 (m, 1 H) 3.94 (s, 3 H) 2.97 (br d, J=5.77 Hz, 2 H) 2.76 (br t, J=6.90 Hz, 2 H) 1.93 (br t, J=6.65 Hz, 2 H).
  • 42
  • [ 22245-92-7 ]
  • N-(1-(4-fluorobenzyl)-6,8-dimethyl-2,3,4,5-tetrahydro-1H-benzazepine-7-yl)-2-(1-methylcyclopropyl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: trimethylphenylammonium perbromide; calcium carbonate / methanol; dichloromethane / 0.5 h / 20 °C 2.1: potassium carbonate; tetrakis-(triphenylphosphine)-palladium / 1,4-dioxane / 120 °C / Inert atmosphere 3.1: sodium hydride / tetrahydrofuran / 0.17 h / 20 °C / Inert atmosphere 3.2: 1 h / 20 °C / Inert atmosphere 4.1: lithium aluminium hydride / tetrahydrofuran / 1 h / 0 - 70 °C 5.1: O-(7-azabenzotriazol-1-yl)-n,n,n',n'-tetramethyluronium hexafluoro-phosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 18 h / 20 °C
  • 43
  • [ 22245-92-7 ]
  • C17H19ClN2OS [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: trimethylphenylammonium perbromide; calcium carbonate / methanol; dichloromethane / 0.5 h / 20 °C 2.1: potassium carbonate; tetrakis-(triphenylphosphine)-palladium / 1,4-dioxane / 120 °C / Inert atmosphere 3.1: sodium hydride / tetrahydrofuran / 0.17 h / 60 °C / Inert atmosphere 3.2: 1.83 h / 60 °C / Inert atmosphere
  • 44
  • [ 22245-92-7 ]
  • (1-(5-chlorothiophene-2-yl)methyl)-6,8-dimethyl-2,3,4,5-tetrahydro-1H-benzazepine-7-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: trimethylphenylammonium perbromide; calcium carbonate / methanol; dichloromethane / 0.5 h / 20 °C 2.1: potassium carbonate; tetrakis-(triphenylphosphine)-palladium / 1,4-dioxane / 120 °C / Inert atmosphere 3.1: sodium hydride / tetrahydrofuran / 0.17 h / 60 °C / Inert atmosphere 3.2: 1.83 h / 60 °C / Inert atmosphere 4.1: borane-THF / tetrahydrofuran / 1 h / 70 °C
  • 45
  • [ 22245-92-7 ]
  • C17H19FN2OS [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: trimethylphenylammonium perbromide; calcium carbonate / methanol; dichloromethane / 0.5 h / 20 °C 2.1: potassium carbonate; tetrakis-(triphenylphosphine)-palladium / 1,4-dioxane / 120 °C / Inert atmosphere 3.1: sodium hydride / tetrahydrofuran; N,N-dimethyl-formamide / 0.17 h / 60 °C / Inert atmosphere 3.2: 0.83 h / 60 °C / Inert atmosphere
  • 46
  • [ 22245-92-7 ]
  • C17H21FN2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: trimethylphenylammonium perbromide; calcium carbonate / methanol; dichloromethane / 0.5 h / 20 °C 2.1: potassium carbonate; tetrakis-(triphenylphosphine)-palladium / 1,4-dioxane / 120 °C / Inert atmosphere 3.1: sodium hydride / tetrahydrofuran; N,N-dimethyl-formamide / 0.17 h / 60 °C / Inert atmosphere 3.2: 0.83 h / 60 °C / Inert atmosphere 4.1: borane-THF / tetrahydrofuran / 1 h / 70 °C
  • 47
  • [ 22245-92-7 ]
  • C19H21ClN2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: trimethylphenylammonium perbromide; calcium carbonate / methanol; dichloromethane / 0.5 h / 20 °C 2.1: potassium carbonate; tetrakis-(triphenylphosphine)-palladium / 1,4-dioxane / 120 °C / Inert atmosphere 3.1: sodium hydride / N,N-dimethyl-formamide / 0.17 h / 20 °C / Inert atmosphere 3.2: 0.83 h / 20 °C / Inert atmosphere
  • 48
  • [ 22245-92-7 ]
  • C19H23ClN2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: trimethylphenylammonium perbromide; calcium carbonate / methanol; dichloromethane / 0.5 h / 20 °C 2.1: potassium carbonate; tetrakis-(triphenylphosphine)-palladium / 1,4-dioxane / 120 °C / Inert atmosphere 3.1: sodium hydride / N,N-dimethyl-formamide / 0.17 h / 20 °C / Inert atmosphere 3.2: 0.83 h / 20 °C / Inert atmosphere 4.1: BH3 / tetrahydrofuran / 2 h / 70 °C
  • 49
  • [ 22245-92-7 ]
  • C19H21BrN2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: trimethylphenylammonium perbromide; calcium carbonate / methanol; dichloromethane / 0.5 h / 20 °C 2.1: potassium carbonate; tetrakis-(triphenylphosphine)-palladium / 1,4-dioxane / 120 °C / Inert atmosphere 3.1: sodium hydride / N,N-dimethyl-formamide / 0.17 h / 20 °C / Inert atmosphere 3.2: 0.83 h / 20 °C / Inert atmosphere
  • 50
  • [ 22245-92-7 ]
  • 7-amino-6,8-dibromo-1,3,4,5-tetrahydro-2H-1-benzazepine-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
95% With trimethylphenylammonium perbromide; calcium carbonate In methanol; dichloromethane at 20℃; for 0.5h; 1.3 Step 3: 7-amino-6,8-dibromo-1,3,4,5-tetrahydro-2H-1-benzazepine-2-one (Compound 4) Compound 3 (500 mg, 2.8 mmol), methanol (20 mL), dichloromethane (50 mL), benzyltrimethylammonium tribromide (2.2 g, 5.6 mmol) and calcium carbonate (2.5 g, 7.06 mmol) were added to 100mL eggplant-shaped flask, the mixture was reacted at room temperature for 30 minutes, then filtered, concentrated to remove the solvent, and the residue was purified by column chromatography to obtain compound 4 (900 mg, yield: 95%). MS (ESI): Calcd. for C10H10Br2N2O 332; Found 333 [M+H]+.
95% With trimethylphenylammonium perbromide; calcium carbonate In methanol; dichloromethane at 20℃; for 0.5h; 1.3 Step 3: 7-amino-6,8-dibromo-1,3,4,5-tetrahydro-2H-1-benzazepine-2-one (Compound 4) Compound 3 (500 mg, 2.8 mmol), methanol (20 mL), dichloromethane (50 mL), benzyltrimethylammonium tribromide (2.2 g, 5.6 mmol) and calcium carbonate (2.5 g, 7.06 mmol) were added to 100mL eggplant-shaped flask, the mixture was reacted at room temperature for 30 minutes, then filtered, concentrated to remove the solvent, and the residue was purified by column chromatography to obtain compound 4 (900 mg, yield: 95%). MS (ESI): Calcd. for C10H10Br2N2O 332; Found 333 [M+H]+.
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