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[ CAS No. 869363-13-3 ] {[proInfo.proName]}

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Chemical Structure| 869363-13-3
Chemical Structure| 869363-13-3
Structure of 869363-13-3 * Storage: {[proInfo.prStorage]}
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Product Details of [ 869363-13-3 ]

CAS No. :869363-13-3 MDL No. :MFCD11840561
Formula : C25H15ClF2N4O2 Boiling Point : -
Linear Structure Formula :- InChI Key :HHFBDROWDBDFBR-UHFFFAOYSA-N
M.W : 476.86 Pubchem ID :11712649
Synonyms :

Safety of [ 869363-13-3 ]

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 [ 869363-13-3 ]

* 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 [ 869363-13-3 ]

[ 869363-13-3 ] Synthesis Path-Downstream   1~18

  • 1
  • (E)-8-chloro-1-(2,6-difluorophenyl)-4-((dimethylamino)methylene)-3H-benzo[c]azepin-5(4H)-one [ No CAS ]
  • [ 42823-46-1 ]
  • [ 869363-13-3 ]
YieldReaction ConditionsOperation in experiment
42% 4-[9-Chloro-7-(2,6-difluoro-phenyl)-5H-benzo[c]pyrimido[4,5-e]azepin-2-ylamino]-benzoic acid (I-135) Method R: 8-Chloro-4-dimethylaminomethylene-1-(2,6-difluoro-phenyl)-3,4-dihydro-benzo[c]azepin-5-one (5aa) (2.6 g, 7.1 mmol), 4-guanidino-benzoic acid hydrochloride (1.7 g, 7.8 mmol) and K2CO3.1.5H2O (2.6 g, 15.6 mmol) in EtOH (50 mL) were refluxed for 14 h. The mixture was cooled and then poured into H2O (400 mL). While stirring, 1N HCl was added dropwise to pH=3. EtOAc (400 mL) was then added and the organic portion was washed with H2O (2×100 mL), dried over Na2SO4 and concentrated to dryness in vacuo. The residue was suspended in CH2Cl2 and filtered. The solids were dissolved in EtOAc, filtered through silica gel, concentrated to dryness in vacuo and dried under vacuum to yield 1-135 as a white solid (1.4 g, 42%).
  • 2
  • [ 869363-13-3 ]
  • 4-[9-Chloro-7-(2,6-difluoro-phenyl)-7H-benzo[c]pyrimido[4,5-e]azepin-2-ylamino]-benzoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
30% Stage #1: 4-[9-chloro-7-(2,6-difluorophenyl)-5H-pyrimido[5,4-d][2]benzazepin-2-yl]amino}benzoic acid With potassium <i>tert</i>-butylate In tetrahydrofuran for 1h; Stage #2: With hydrogenchloride In tetrahydrofuran; water 20.Z Method Z for the Synthesis of Compounds of the Formula (I) 4-[9-Chloro-7-(2,6-difluoro-phenyl)-7H-benzo[c]pyrimido[4,5-e]azepin-2-ylamino]-benzoic acid (I-387). To a solution of I-135 (1.0 g, 2.1 mmol) in THF (20 mL) was added potassium tert-butoxide (1M in THF, 21 mmol). The solution was allowed to stir for 1 hr and then the pH was adjusted to 3 with 1N HCl. The solution was then diluted with water (100 mL) and extracted with EtOAc (3×50 mL). The organic portion was dried (Na2SO4), concentrated in vacuo and the resulting brown oil purified by RP-HPLC (C18, 0 to 100% CH3CN in water containing 0.1% formic acid) to provide, after lyophilization, I-387 (0.3 g, 30%).
  • 3
  • [ 869363-13-3 ]
  • sodium 4-[9-chloro-7-(2,6-difluorophenyl)-5H-pyrimido[5,4-d][2]benzazepin-2-yl]amino}benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% With sodium hydroxide In ethanol; water for 1h; Inert atmosphere;
72% With sodium hydroxide In ethanol; water at 50 - 70℃; 13.R 4-[9-Chloro-7-(2,6-difluoro-phenyl)-5H-benzo[c]pyrimido[4,5-e]azepin-2-ylamino]-benzoic acid (1-135) (1.5 g, 2.95 mol) was added to a solution of ethanol (8.86 mL) and water (1.2 mL), and the mixture was heated to 50° C. An aqueous NaOH solution (0.02458 g/mL) was added to a target solution pH of 11.6. Additional water was added to a total of 4.26 mL/g of free acid. The resultant slurry was heated to 70° C. and rapidly filtered, maintaining a solution temperature of 65-70° C. Warm ethanol (9.15 mL, 7.21 g) was added, and the solution cooled to 65° C. Seed crystals of the sodium salt of I-135 (7.1 mg, 0.014 mol) were added as a slurry in 10% (wt) solution of 75:25 ethanol:water. The mixture was maintained at 65° C. for one hour, and then was cooled to 35° C. at a rate of 12° C./hour. At 35° C., a second addition of ethanol (4.72 g, 5.98 mL) was performed. The mixture was cooled to 0° C. at a rate of 12° C./hour, and then held at 0° C. for one hour. The resultant thick slurry was filtered, and the wet filter cake was rinsed with cold ethanol (5.52 g, 7 mL) to afford a 72% yield of the sodium salt of 1-135, as a hydrate
  • 4
  • [ 869363-13-3 ]
  • allyl glucuronate [ No CAS ]
  • C34H27ClF2N4O8 [ No CAS ]
YieldReaction ConditionsOperation in experiment
9% With 4-methyl-morpholine; HATU In acetonitrile for 2h; Inert atmosphere;
  • 5
  • [ 869363-13-3 ]
  • [ 1393381-46-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.5 h / 20 °C / Inert atmosphere 1.2: 3 h / 20 °C / Inert atmosphere 2.1: trifluoroacetic acid / dichloromethane / 0 - 20 °C / Inert atmosphere
  • 6
  • [ 869363-13-3 ]
  • (E)-cyclooct-4-en-1-yl (1-(2-(4-((9-chloro-7-(2,6-difluorophenyl)-5H-benzo[c]pyrimido[4,5-e]azepin-2-yl)amino)benzamido)ethyl)piperidin-4-yl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.5 h / 20 °C / Inert atmosphere 1.2: 3 h / 20 °C / Inert atmosphere 2.1: trifluoroacetic acid / dichloromethane / 0 - 20 °C / Inert atmosphere 3.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 1 h / 20 °C / Inert atmosphere
  • 7
  • [ 869363-13-3 ]
  • tert-butyl (1-(2-aminoethyl)piperidin-4-yl)carbamate [ No CAS ]
  • [ 1393381-45-7 ]
YieldReaction ConditionsOperation in experiment
79% Stage #1: 4-[9-chloro-7-(2,6-difluorophenyl)-5H-pyrimido[5,4-d][2]benzazepin-2-yl]amino}benzoic acid With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 0.5h; Inert atmosphere; Stage #2: tert-butyl (1-(2-aminoethyl)piperidin-4-yl)carbamate In N,N-dimethyl-formamide at 20℃; for 3h; Inert atmosphere;
  • 8
  • [ 869366-03-0 ]
  • [ 869363-13-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: sulfuric acid / dichloromethane / 0 °C / Inert atmosphere 2: toluene / 4 h / 80 °C / Inert atmosphere 3: potassium carbonate / ethanol / 14 h / Inert atmosphere; Reflux
Multi-step reaction with 4 steps 1: hydrogenchloride; water / 1,4-dioxane / 16 h / 20 - 60 °C / Inert atmosphere 2: sodium hydrogencarbonate / water; dichloromethane; 1,4-dioxane / 2 h / Inert atmosphere 3: dichloromethane / 40 °C / Inert atmosphere 4: potassium carbonate sesquihydrate / methanol / 16 h / 55 °C / Inert atmosphere
  • 9
  • [ 869366-09-6 ]
  • [ 869363-13-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: toluene / 4 h / 80 °C / Inert atmosphere 2: potassium carbonate / ethanol / 14 h / Inert atmosphere; Reflux
Multi-step reaction with 2 steps 1: dichloromethane / 40 °C / Inert atmosphere 2: potassium carbonate sesquihydrate / methanol / 16 h / 55 °C / Inert atmosphere
  • 10
  • [ 869365-92-4 ]
  • [ 869363-13-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: trifluoroacetic acid / dichloromethane / 0 - 20 °C / Inert atmosphere 2.1: hydrogenchloride; acetic acid; sodium nitrite / water / 0 - 5 °C / Inert atmosphere 2.2: 0 - 20 °C / Inert atmosphere 3.1: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride / dichloromethane / 0.5 h / Inert atmosphere 3.2: 16 h / 20 °C / Inert atmosphere 4.1: sulfuric acid / dichloromethane / 0 °C / Inert atmosphere 5.1: toluene / 4 h / 80 °C / Inert atmosphere 6.1: potassium carbonate / ethanol / 14 h / Inert atmosphere; Reflux
  • 13
  • [ 18437-66-6 ]
  • [ 869363-13-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: tert.-butyl lithium / tetrahydrofuran; pentane / 3.33 h / -78 - -30 °C / Inert atmosphere 1.2: 0.83 h / -78 °C / Inert atmosphere 2.1: trifluoroacetic acid / dichloromethane / 0 - 20 °C / Inert atmosphere 3.1: hydrogenchloride; acetic acid; sodium nitrite / water / 0 - 5 °C / Inert atmosphere 3.2: 0 - 20 °C / Inert atmosphere 4.1: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride / dichloromethane / 0.5 h / Inert atmosphere 4.2: 16 h / 20 °C / Inert atmosphere 5.1: sulfuric acid / dichloromethane / 0 °C / Inert atmosphere 6.1: toluene / 4 h / 80 °C / Inert atmosphere 7.1: potassium carbonate / ethanol / 14 h / Inert atmosphere; Reflux
  • 14
  • [ 18063-02-0 ]
  • [ 869363-13-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: tert.-butyl lithium / tetrahydrofuran; pentane / 3.33 h / -78 - -30 °C / Inert atmosphere 1.2: 0.83 h / -78 °C / Inert atmosphere 2.1: trifluoroacetic acid / dichloromethane / 0 - 20 °C / Inert atmosphere 3.1: hydrogenchloride; acetic acid; sodium nitrite / water / 0 - 5 °C / Inert atmosphere 3.2: 0 - 20 °C / Inert atmosphere 4.1: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride / dichloromethane / 0.5 h / Inert atmosphere 4.2: 16 h / 20 °C / Inert atmosphere 5.1: sulfuric acid / dichloromethane / 0 °C / Inert atmosphere 6.1: toluene / 4 h / 80 °C / Inert atmosphere 7.1: potassium carbonate / ethanol / 14 h / Inert atmosphere; Reflux
  • 15
  • [ 869366-10-9 ]
  • [ 42823-46-1 ]
  • [ 869363-13-3 ]
  • 16
  • C16H12ClF2NO2 [ No CAS ]
  • [ 869363-13-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: sodium hydrogencarbonate / water; dichloromethane; 1,4-dioxane / 2 h / Inert atmosphere 2: dichloromethane / 40 °C / Inert atmosphere 3: potassium carbonate sesquihydrate / methanol / 16 h / 55 °C / Inert atmosphere
  • 17
  • [ 869363-13-3 ]
  • 4-amino-N-(2-(2,6-dioxopiperidin-3-yl)-1-oxoisoindolin-4-yl)butanamide [ No CAS ]
  • C42H33ClF2N8O5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 20℃; Cooling with ice; Inert atmosphere; 2.2.1 (2.2) Preparation of TED molecule 2 Weigh compound UBI-1005 (20mg, 0.042mmol) was dissolved in DMF (2mL), was added under ice-water bath successively NH22-Linker (Ll) -B2 (1 eq.), Of HATU (2eq.32mg, 0.084 mmol) and DIEA (3eq. 16.2 mg, 0.126 mmol).After the addition was completed, the material system was stirred at room temperature for 18 hours under nitrogen protection. After the reaction was completed, the reaction solution was poured into 5 mL of water and extracted three times with ethyl acetate (5 mL * 3). The organic phases were combined and washed with saturated brine, anhydrous Na2SO4 wasdried, concentrated by rotary evaporation under reduced pressure, and the crude product was obtained. The corresponding TED compound was prepared by thin layer chromatography silica gel plate separation with the polarity of the developing agent (DCM / MeOH = 10/1).
  • 18
  • [ 869363-13-3 ]
  • (2S,4R)-1-((S)-2-(4-aminobutanamido)-3,3-dimethylbutanoyl)-4-hydroxy-N-(4-(4-methylthiazol-5-yl)benzyl)pyrrolidine-2-carboxamide [ No CAS ]
  • C51H50ClF2N9O5S [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 20℃; Cooling with ice; Inert atmosphere; 2.2.2 (2.2) Preparation of TED molecule 2 Weigh compound UBI-1005 (20mg, 0.042mmol) was dissolved in DMF (2mL), was added under ice-water bath successively NH22-Linker (Ll) -B2 (1 eq.), Of HATU (2eq.32mg, 0.084 mmol) and DIEA (3eq. 16.2 mg, 0.126 mmol).After the addition was completed, the material system was stirred at room temperature for 18 hours under nitrogen protection. After the reaction was completed, the reaction solution was poured into 5 mL of water and extracted three times with ethyl acetate (5 mL * 3). The organic phases were combined and washed with saturated brine, anhydrous Na2SO4 wasdried, concentrated by rotary evaporation under reduced pressure, and the crude product was obtained. The corresponding TED compound was prepared by thin layer chromatography silica gel plate separation with the polarity of the developing agent (DCM / MeOH = 10/1).
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