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[ CAS No. 207989-90-0 ] {[proInfo.proName]}

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Product Details of [ 207989-90-0 ]

CAS No. :207989-90-0 MDL No. :MFCD15527558
Formula : C10H10BrNO Boiling Point : -
Linear Structure Formula :- InChI Key :PFJCJXIUAVSTJB-UHFFFAOYSA-N
M.W : 240.10 Pubchem ID :12056595
Synonyms :

Calculated chemistry of [ 207989-90-0 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.3
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 58.33
TPSA : 29.1 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.47 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.1
Log Po/w (XLOGP3) : 1.83
Log Po/w (WLOGP) : 1.69
Log Po/w (MLOGP) : 2.19
Log Po/w (SILICOS-IT) : 2.83
Consensus Log Po/w : 2.13

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.76
Solubility : 0.42 mg/ml ; 0.00175 mol/l
Class : Soluble
Log S (Ali) : -2.06
Solubility : 2.08 mg/ml ; 0.00868 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.08
Solubility : 0.0202 mg/ml ; 0.0000841 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.73

Safety of [ 207989-90-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280 UN#:N/A
Hazard Statements:H302-H317 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 207989-90-0 ]

* 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 [ 207989-90-0 ]

[ 207989-90-0 ] Synthesis Path-Downstream   1~18

  • 1
  • [ 207989-90-0 ]
  • [ 890005-22-8 ]
  • 5-{4-[3-(trifluoromethyl)-4,5,6,7-tetrahydro-1H-indazol-1-yl]phenyl}-2-pyrrolidinone [ No CAS ]
YieldReaction ConditionsOperation in experiment
14% With potassium carbonate;copper(l) iodide; dimethylaminoacetic acid; In dimethyl sulfoxide; at 190.0℃; for 0.5h;Microwave; A mixture of <strong>[207989-90-0]5-(4-bromophenyl)-2-pyrrolidinone</strong> (81 mg, 0.34mmol; preparation described in WO00/21958), 3-(trifluoromethyl)-4,5,6,7-tetrahydro-1/-/-indazole (64mg, 0.34mmol) N,N-dimethylglycine (20mol%, 7mg, 0.07mmol), copper (I) iodide (10mol%, 6.5mg, 0.034mmol) and potassium carbonate (0.7mmol, 97mg) in dimethylsulfoxide (2ml) was stirred at 19O0C in a microwave reactor for 30 minutes. The reaction mix was cooled and partitioned between dichloromethane (5ml) and water (5ml). The organic layer was added to a 5g isolute silica sep-pak column and eluted with ethyl acetate. The solvent was removed under reduced pressure to give a dark oil (161 mg) which was further purified by mass directed auto-prep (MDAP) to give the title compound as a yellow oil (17mg, 14%). LC/Mass Spec (ES): Found 350 (ES+), retention time 2.99mins. Ci8H18F3N3O requires 349.1 H-NMR (400MHz, CDCI3): 1.83 (4H, m), 1.97 (1 H, m), 2.48 (2H, m), 2.52 (1 H, m), 2.70 (4H, m), 4.83 (1 H, t, J=7Hz), 6.13 (1 H, bs), 7.40 (2H, m), 7.51 (2H, m).
YieldReaction ConditionsOperation in experiment
Example XI-3 In a 3 l three-necked flask fitted with stirrer and distillation bridge, 199.3 g of ammonium formate were initially charged in 127.9 g of formic acid, and 210 g of 4-bromobenzoylpropionic acid which had been recrystallized from toluene were added. The flask was then immersed in an oil bath which was at 200 C. At 60 C., the content of the flask starts to dissolve with evolution of gas. Over a period of approximately 2 h, the mixture is distilled, at a bottom temperature which increases from 140 to 167 C. After cooling to below 60 C., 1 l of dichloromethane was added carefully, and salt which had precipitated out was separated off by filtration with suction using a nutsch filter. The organic phase was washed with 1 l of water, dried over magnesium sulphate and concentrated under reduced pressure. For purification, the crude product was filtered through 1 kg of silica gel using dichloromethane/ethanol/triethylamine (95:5:3) and subsequently crystallized from methyl tert-butyl ether. This gave 38 g (19% of theory) of gamma-4-bromophenyl-gamma-butyrolactam of melting point 142 C.
Example XI-3 In a 3l three-necked flask fitted with stirrer and distillation bridge, 199.3 g of ammonium formate were initially charged in 127.9g.of formic acid, and 210g of 4-bromobenzoylpropionic acid which had been recrystallized from toluene were added. The flask was then immersed in an oil bath which was at 200 C. At 60 C., the content of the flask starts to dissolve with evolution of gas. Over a period of approximately 2 h, the mixture is distilled, at a bottom temperature which increases from 140 to 167 C. After cooling to below 60 C., 1 1 of dichloromethane was added carefully, and salt which had precipitated out was separated off by filtration with suction using a nutsch filter. The organic phase was washed with 1 1 of water, dried over magnesium sulphate and concentrated under reduced pressure. For purification, the crude product was filtered through 1 kg of silica gel using dichloromethane/ethanol/triethylamine (95:5:3) and subsequently crystallized from methyl tert-butyl ether. This gave 38 g (19% of theory) of gamma-4-bromophenyl-gamma-butyrolactam of melting point 142 C.
EXAMPLE XI-3 In a 3 l three-neck flask fitted with stirrer and distillation link, 199.3 g of ammonium formate in 127.9 g of formic acid were charged initially, and 210 g of 4-bromobenzoylpropionic acid which had been recrystallized from toluene were added. The flask was then immersed into a 200 C. oil bath. At 60 C., the content of the flask began to dissolve with the evolution of gas. For about 2 hours, the mixture was subjected to distillation at a bottom temperature increasing from 140 to 167 C., until the reaction had ended. After cooling to below 60 C., 1 l of dichloromethane was added carefully and precipitated salt was separated off by filtration with suction through a nutsch filter. The organic phase was washed with 1 l of water, dried over magnesium sulphate and concentrated under reduced pressure. For purification, the crude product was filtered through 1 kg of silica gel using dichloromethane/ethanol/triethylamine (95:5:3) and then crystallized from methyl tert-butyl ether. 38 g (19% of theory) of gamma-4-bromophenyl-gamma-butyrolactam of melting point 142 C. were obtained.
  • 3
  • [ 207989-90-0 ]
  • [ 24424-99-5 ]
  • ammonium chloride [ No CAS ]
  • [ 207989-92-2 ]
YieldReaction ConditionsOperation in experiment
With n-butyllithium; diisopropylamine; In tetrahydrofuran; hexane; Example IX-3 At -78 C., 3.24 ml of diisopropylamine were initially charged in 90 ml of THF and admixed with 9.24 ml of a 2.4 N solution of butyllithium in n-hexane. The mixture was stirred at this temperature for 1/2 h, and a solution of 5.02 g of gamma-4-bromophenyl-gamma-butyrolactam (for example from Example XI-3) in 20 ml of THF was then added dropwise. The mixture was stirred at -78 C. for a further 1/2 h, and 5.04 g of di-tert-butyl dicarbonate in 20 ml of THF were then added dropwise, and the mixture was allowed to thaw and stirred at room temperature overnight. The mixture was then hydrolyzed using saturated aqueous ammonium chloride solution, acidified with 2N hydrochloric acid and extracted three times with 150 ml of dichloromethane. The extract was dried over magnesium sulphate and concentrated, and the product was then purified by crystallization from dichloromethane/hexane. This gave a total of 7.61 g (97% of theory) of crystalline N-t-butoxycarbonyl-gamma-4-bromophenyl-gamma-butyrolactam. The crystal fraction of the highest purity (2.34 g) melted at 122-124 C.
With n-butyllithium; diisopropylamine; In tetrahydrofuran; hexane; Example IX-3 At -78 C., 3.24 ml of diisopropylamine were initially charged in 90 ml of THF and admixed with 9.24 ml of a 2.4 N solution of butyllithium in n-hexane. The mixture was stirred at this temperature for 1/2 h, and a solution of 5.02 g of gamma-4-bromophenyl-gamma-butyrolactam (for example from Example XI-3) in 20 ml of THF was then added dropwise. The mixture was stirred at -78 C. for a further 1/2 h, and 5.04 g of di-tert-butyl dicarbonate in 20 ml of THF were then added dropwise, and the mixture was allowed to thaw and stirred at room temperature overnight. The mixture was then hydrolyzed using saturated aqueous ammonium chloride solution, acidified with 2N hydrochloric acid and extracted three times with 150 ml of dichloromethane. The extract was dried over magnesium sulphate and concentrated, and the product was then purified by crystallization from dichloromethane/hexane. This gave a total of 7.61 g (97% of theory) of crystalline N-t-butoxycarbonyl-gamma-4-bromophenyl-gamma-butyrolactam. The crystal fraction of the highest purity (2.34 g) melted at 122-124 C.
  • 4
  • [ 207989-90-0 ]
  • [ 73183-34-3 ]
  • [ 1004294-99-8 ]
YieldReaction ConditionsOperation in experiment
With potassium acetate;1,1'-bis-(diphenylphosphino)ferrocene; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; at 150.0℃; for 0.333333h;Microwave irradiation; EXAMPLE 239 5-(4-(4-r(4-chlorophenyl)sulfanyl]-l-ethvl-l-H-pyrazol-3-yl|phenvl)pyrrolidin-2-oneA solution of <strong>[207989-90-0]5-(4-bromophenyl)pyrrolidin-2-one</strong> (132 mg, 0.548 mmol), bis-pinacolalodiboron (181 mg, 0.713 mmol), KOAc (161 mg, 1.645 mmol), DPPF (15.2 mg, 0.027 mmol) and Pd(dppf)Cl2 (20 mg, 0.027 mmol) in 1,4-dioxane (2 mL) was microwaved at 150C for 20 min. Upon completion of the reaction as judged by LC/MS analysis, Intermediate 64 (200 mg, 0.548 mmol), PdCl2(PPh3)2 (38.5 mg, 0.055 mmol), and 2M Na2CO3 (0.548 mL, 1.097 mmol) were added to the solution and heated at 1100C for 36 h. Upon completion of the reaction, the solution was diluted with EtOAc (2OmL) and water (2OmL). The two layers were partitioned and the aqueous phase was re-extracted with EtOAc (2OmL). The organic layers were combined, dried over MgSO4, filtered and concentrated giving rise to a black oil. The oil was purified by chromatography on silica gel, eluting with EtOAc / Hexane to afford the title compound (35 mg). LC/MS: m/e 398.07 (M+H). 1H NMR (500 MHz, CDCl3): delta 7.89 (2H, d, J = 8.5 Hz), 7.65 (IH, s), 7.28 (2H, t), 7.18 (2H, d, J = 9.0 Hz), 7.01 (2H, d} J - 8.5 Hz), 5.86 (IH, s), 4.76 (IH, m), 4.28 (2H3 q), 2.58 (IH, m), 2.45 (2H, m), 2.0 (IH1 m), 1.59 (3H, t).
  • 5
  • [ 207989-90-0 ]
  • [ 1199802-98-6 ]
  • 6
  • [ 207989-90-0 ]
  • [ 1199802-99-7 ]
  • 11
  • N-[{3,5-bis(trifluoromethyl)benzoyl}oxy]-4-(4-bromophenyl)butanamide [ No CAS ]
  • [ 207989-90-0 ]
  • 12
  • [ 108-86-1 ]
  • [ 207989-90-0 ]
  • 13
  • [ 6340-79-0 ]
  • [ 207989-90-0 ]
  • 14
  • [ 30913-86-1 ]
  • [ 207989-90-0 ]
  • 15
  • methyl 4-(4-bromophenyl)-4-(hydroxyimino)butanoate [ No CAS ]
  • [ 207989-90-0 ]
YieldReaction ConditionsOperation in experiment
69.4% With zinc; In methanol; at 80.0℃; for 16.0h;Inert atmosphere; To a solution of methyl-4- (4-bromophenyl)-4-(hydroxyimino) butanoate (11.2 g, 39.16 mmol) in CH 3OH (100 mL) was added Zn (powder, 5.2 g, 78.32 mmol), the mixture was stirred in a 80C oil bath under N 2 for about 16h. Cooled to ambient temperature, filtered, the filtrate was concentrated. The residue was partitioned between DCM (500 mL) and Sat. NaHCO 3 (300 mL). The organic layer was separated, concentrated to give the crude product, which was slurry with PE (100 mL) to give the product as white solid. (6.5 g, 69.4%). [M+1] + 240.0, 241.9.
  • 16
  • [ 207989-90-0 ]
  • tert-butyl 3-((1H-pyrrolo[2,3-b]pyridin-5-yl)oxy)-4'-(1-(2-bromophenyl)-5-oxopyrrolidin-2-yl)-[1,1'-biphenyl]-4-carboxylate [ No CAS ]
  • 17
  • [ 207989-90-0 ]
  • tert-butyl 3-((1H-pyrrolo[2,3-b]pyridin-5-yl)oxy)-4'-(1-(2-cyclopropylphenyl)-5-oxopyrrolidin-2-yl)-[1,1'-biphenyl]-4-carboxylate [ No CAS ]
  • 18
  • [ 207989-90-0 ]
  • tert-butyl 2-((1H-pyrrolo[2,3-b]pyridin-5-yl)oxy)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate [ No CAS ]
  • tert-butyl 3-((1H-pyrrolo[2,3-b]pyridin-5-yl)oxy)-4'-(5-oxopyrrolidin-2-yl)-[1,1'-biphenyl]-4-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; In 1,4-dioxane; at 80.0℃; for 18.0h;Inert atmosphere; To a solution of tert-butyl 2- ((1H-pyrrolo [2, 3-b] pyridin-5-yl) oxy)-4-(4, 4, 5, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) benzoate (2.2 g, 5.00 mmol) in 1, 4-dioxane (50 mL) was added 5- (4-bromophenyl) pyrrolidin-2-one (1.2 g, 5.00 mmol), Pd (dppf) Cl 2 (183 mg, 0.25 mmol) and 1 N K 2CO 3 (15 mL), the mixture was stirred in a 80C oil bath under N 2 for about 18h. Cooled to r.t, extracted with DCM (50 mL2). The combined organic layers were concentrated and purified by column chromatograph on silica gel (100-200 mesh, eluent: MeOH: DCM= 1: 10) to give the crude product as brown solid. (2.4 g). [M+1] + 469.8.
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