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[ CAS No. 1036389-05-5 ] {[proInfo.proName]}

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Product Details of [ 1036389-05-5 ]

CAS No. :1036389-05-5 MDL No. :MFCD24119832
Formula : C8H7BrFNO2 Boiling Point : -
Linear Structure Formula :- InChI Key :LBZFEFCDWYLWCF-UHFFFAOYSA-N
M.W : 248.05 Pubchem ID :68759053
Synonyms :

Calculated chemistry of [ 1036389-05-5 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 49.78
TPSA : 52.32 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
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) : 1.89
Log Po/w (XLOGP3) : 1.89
Log Po/w (WLOGP) : 2.39
Log Po/w (MLOGP) : 2.48
Log Po/w (SILICOS-IT) : 2.09
Consensus Log Po/w : 2.15

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.78
Solubility : 0.413 mg/ml ; 0.00167 mol/l
Class : Soluble
Log S (Ali) : -2.61
Solubility : 0.607 mg/ml ; 0.00245 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.25
Solubility : 0.139 mg/ml ; 0.00056 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.75

Safety of [ 1036389-05-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P264-P280-P302+P352-P305+P351+P338-P332+P313-P337+P313-P362 UN#:N/A
Hazard Statements:H315-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1036389-05-5 ]

* 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 [ 1036389-05-5 ]

[ 1036389-05-5 ] Synthesis Path-Downstream   1~19

  • 1
  • [ 1036389-05-5 ]
  • [ 1036390-96-1 ]
  • [ 544-92-3 ]
  • [ 1036389-07-7 ]
  • [ 1036390-98-3 ]
YieldReaction ConditionsOperation in experiment
In N,N-dimethyl-formamide at 160℃; for 0.25h; 9.C 9B (0.9 g, 3.6 mmol) was dissolved into DMF (25 mL). Cu(I)CN(3.45 g, 38.5 mmol) was added and the resulting mixture heated at 160 0C for 15 min. under argon. The reaction was cooled to rt., quenched with a 50/50 mix NH4OHZH2O (50 mL), stirred 5 min and filtered through Celite . The filter cake was washed with EtOAc (3 x 50 mL) and the combined organics were extracted with water (3 x 100 mL), brine and dried with MgSO4. The combined organics were concentrated and purified on preparatory HPLC to yield 9C (570mg, 2.9mmol) in a 1 : 1 mixture with a regioisomers in 81% yield MS (ESI) M/Z 195.2 (M+H)
  • 2
  • [ 67-56-1 ]
  • [ 881415-28-7 ]
  • [ 881415-27-6 ]
  • [ 1036389-05-5 ]
  • [ 1036390-96-1 ]
YieldReaction ConditionsOperation in experiment
9A (3.7g, 14 mmol) was refluxed for 1 h in thionyl chloride (15 mL) and concentrated to an oil. MeOH (40 mL) was added slowly to the residue and the mixture refluxed for 1 h. The reaction was concentrated to dryness. The residue was heated at 90 0C for 4 h in acetic acid (20 mL) with a Fe powder (365 mg, 6.7 mmol). Upon cooling to rt the reaction was diluted with EtOAc (100 mL) and the resulting mixture filtered through Celite . The filter cake was washed with EtOAc (3 x 100 mL). The combined organics were washed with water and brine, dried w/ MgSO4 and concentrated to give 9B (2.Og, 54% yield) in a 1: 1 mixture with a regioisomers. MS (ESI) mk 248.1 (M+H)
  • 3
  • [ 67-56-1 ]
  • [ 132715-69-6 ]
  • [ 1036389-05-5 ]
  • [ 1036390-96-1 ]
YieldReaction ConditionsOperation in experiment
27%; 53% In an ice bath, fuming nitric acid (2mL, 22.83mmoL) was added dropwise 2-bromo-3-fluoro - benzoic acid (5g, 22.8mmol) and concentrated sulfuric acid (15mL) in the mixed solution.After the addition was complete, brought to room temperature stirred for 2 hours.Poured into ice water, a large number of solid was filtered, the solid washed with water and dried under high vacuum, a white solid 5.3g, mixture of intermediate 4c and 4e, (4c / 4e = 2/1), in a yield of 88%.Most of this mixture was used directly in the next reaction, a small amount was purified by column chromatography and identified as follows: Except that Intermediate 4e Intermediate 4c and 4b was used instead of Intermediate outside Intermediate 5c and 5e intermediates for preparing the same mixture of intermediate 5b, the target was a red-brown product in a yield of 100%, was used directly in the next step. A mixture of 2-bromo-6-fluoro-3-nitrobenzoic acid (Intermediate 4b, 2.5g, 9.5mmoL) was added to thionyl chloride (11.0 mL of) was heated under reflux for 1 hour.Volatile matter was distilled off under reduced pressure, the residue was added to anhydrous methanol (30 mL) was heated at reflux for 1 hour.The solvent was distilled off under reduced pressure, and dried under high vacuum to give a white solid 2.5g, 96% yield.It was used directly in the next step. Except that a mixture of Intermediate 5c and 5e instead of Intermediate Intermediate 5b outside 6c Intermediate and Intermediate 6e a mixture prepared with intermediate 6b.The product was purified by column chromatography to give Intermediate 6c Intermediate 6e and pure. A mixture of 2-bromo-6-fluoro-3-nitrobenzoate (Intermediate 5b, 2.5g, 9.0mmoL), reduced iron powder (1.0g, 17.8 mmoL) was added to glacial acetic acid (13.0 mL) and heated was refluxed for 2 hours, TLC the reaction was complete.Filtered through Celite, washed with ethyl acetate, the solvent was distilled off under reduced pressure.The residue was added to ethyl acetate (30 mL) and water (10 mL), and separated, the solvent was distilled off under reduced pressure, the residue was purified by flash column chromatography, eluted with petroleum ether / ethyl acetate = 10/1, to give a colorless liquid 1.7g, 70% yield.
  • 5
  • [ 132715-69-6 ]
  • [ 1036389-05-5 ]
  • 6
  • [ 881415-28-7 ]
  • [ 1036389-05-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: thionyl chloride / 0.5 h / 0 °C / Inert atmosphere 1.2: 18 h / 60 °C / Inert atmosphere 2.1: iron; acetic acid / water; ethanol / 1 h / 110 °C
  • 7
  • [ 881415-30-1 ]
  • [ 1036389-05-5 ]
YieldReaction ConditionsOperation in experiment
47% With iron; ammonium chloride In ethanol at 80℃; for 4h; 2-3-5 To a solution of a methyl 2-bromo-3-fluoro-5-nitrobenzoate (4.3 g, 15.5 mmol) in EtOH (30 mL) was added Fe powder (8.4 g, 0.15 mol) and sat. NH4Cl (10 mL), the resulting mixture was stirred at 80oC for 4h. Then the solid was removed by filtration, and the filtrate was poured into water, extracted with EtOAc. The combined organic phase was washed with water, brine, concentrated in vacuo to give a residue, which was purified by silica chromatography (1008) (PE/EtOAc (50/1 to 10/1)) to give methyl 5-amino-2-bromo-3-fluorobenzoate (1.8 g, yield 47%) as a yellow solid.1H NMR (400 MHz, DMSO-d6): d 6.81 (d, J = 1.8 Hz, 1H), 6.63 (dd, J = 11.4, 2.6 Hz, 1H), 5.89 (s, 2H), 3.82 (d, J = 6.3 Hz, 3H) ppm.
With iron; acetic acid In ethanol; water at 110℃; for 1h;
  • 8
  • [ 1036389-05-5 ]
  • [ 1036389-09-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N,N-dimethyl-formamide / 0.17 h / Microwave irradiation 2: hydrogen; ammonia / methanol / 16 h / 2585.81 Torr
  • 9
  • [ 1036389-05-5 ]
  • methyl 3-(1-(2-(3,4-dimethoxyphenyl)-2-(7-fluoro-3-oxoisoindolin-5-ylamino)acetyl)pyrrolidin-2-yl)-4-(isopropylsulfonyl)phenylcarbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: N,N-dimethyl-formamide / 0.17 h / Microwave irradiation 2: hydrogen; ammonia / methanol / 16 h / 2585.81 Torr 3: N,N-dimethyl-formamide; acetonitrile; water / Microwave irradiation; Heating 4: N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; 1-hydroxy-7-aza-benzotriazole; N-ethyl-N,N-diisopropylamine / dichloromethane / 20 °C / Inert atmosphere
  • 10
  • [ 1036389-05-5 ]
  • [ 1036389-11-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: N,N-dimethyl-formamide / 0.17 h / Microwave irradiation 2: hydrogen; ammonia / methanol / 16 h / 2585.81 Torr 3: N,N-dimethyl-formamide; acetonitrile; water / Microwave irradiation; Heating
  • 11
  • [ 1036389-05-5 ]
  • [ 108-24-7 ]
  • methyl 5-acetamido-2-bromo-3-fluorobenzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
6.5 g With dmap In tetrahydrofuran at 20℃; for 2h; 1 Step 1. Acetic anhydride (12.4 g, 121 mmol) and DMAP (2.47g, 20.2 mmol) were added to a solution of methyl 5-amino-2-bromo-3-fluorobenzoate (Intermediate 13, 10.0 g, 40.5 mmol) in THF (100 ml_) and the mixture was stirred at rt for 2 h. Saturated aqueous NaHCOs solution (100 ml_) and EtOAc (70 ml_) were added and the phases were separated. The aqueous phase was extracted with EtOAc (2 x 100 ml_), the combined organic phases were dried (Na2S04) and concentrated in vacuo. The residue was triturated with DCM:MeOH (8: 1 , 45 ml_) to yield methyl 5- acetamido-2-bromo-3-fluorobenzoate (6.50 g, 22.4 mmol) as a light yellow solid. LCMS (Method 2): m/z 292.0 (ES+), at 2.05 min.1H NMR: (400 MHz, DMSO-de) d 10.45 (s, 1 H), 7.86 (dd, J = 1 1 .0, 2.4 Hz, 1 H), 7.78 (dd, J = 2.5, 1 .3 Hz, 1 H), 3.88 (s, 3H), 2.07 (s, 3H).
  • 12
  • [ 1036389-05-5 ]
  • 5-acetamido-3-fluoro-2-(2H-1,2,3-triazol-2-yl)benzoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: dmap / tetrahydrofuran / 2 h / 20 °C 2.1: caesium carbonate; cis-N,N'-dimethyl-1,2-diaminocyclohexane / N,N-dimethyl-formamide / 0.33 h / 20 °C / Inert atmosphere 2.2: 16 h / 110 °C / Inert atmosphere
  • 13
  • 2-amino-3-fluoro-5-nitrobenzoic acid [ No CAS ]
  • [ 1036389-05-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: thionyl chloride / 70 °C 2: tert.-butylnitrite; copper(I) bromide / acetonitrile / 70 °C 3: ammonium chloride; iron / ethanol / 4 h / 80 °C
  • 14
  • methy 2-amino-3-fluoro-5-nitrobenzoate [ No CAS ]
  • [ 1036389-05-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: tert.-butylnitrite; copper(I) bromide / acetonitrile / 70 °C 2: ammonium chloride; iron / ethanol / 4 h / 80 °C
  • 15
  • [ 1036389-05-5 ]
  • 7-fluoro-5-((4-(pentan-3-ylamino)-5-(trifluoromethyl)pyrimidin-2-yl)amino)benzo[c][1,2]oxaborol-1(3H)-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: zinc(II) chloride / tetrahydrofuran; <i>tert</i>-butyl alcohol; 1,2-dichloro-ethane / 1 h / 0 °C 1.2: 24 h / 30 °C 2.1: triethylamine / ethanol / 6 h / 80 °C 3.1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / tetrahydrofuran / 24 h / Inert atmosphere; Reflux 4.1: sodium tetrahydroborate; methanol / 0.5 h / 20 °C
  • 16
  • [ 1036389-05-5 ]
  • methyl 2-bromo-3-fluoro-5-((4-(pentan-3-ylamino)-5-(trifluoromethyl)pyrimidin-2-yl)amino)benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: zinc(II) chloride / tetrahydrofuran; <i>tert</i>-butyl alcohol; 1,2-dichloro-ethane / 1 h / 0 °C 1.2: 24 h / 30 °C 2.1: triethylamine / ethanol / 6 h / 80 °C
  • 17
  • [ 1036389-05-5 ]
  • methyl 3-fluoro-5-((4-(pentan-3-ylamino)-5-(trifluoromethyl)pyrimidin-2-yl)amino)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: zinc(II) chloride / tetrahydrofuran; <i>tert</i>-butyl alcohol; 1,2-dichloro-ethane / 1 h / 0 °C 1.2: 24 h / 30 °C 2.1: triethylamine / ethanol / 6 h / 80 °C 3.1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / tetrahydrofuran / 24 h / Inert atmosphere; Reflux
  • 18
  • [ 1036389-05-5 ]
  • [ 3932-97-6 ]
  • methyl 2-bromo-5-((4-chloro-5-(trifluoromethyl)pyrimidin-2-yl)amino)-3-fluorobenzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
47% Stage #1: 2,4-dichloro-5-trifluoromethylpyrimidine With zinc(II) chloride In tetrahydrofuran; 1,2-dichloro-ethane; <i>tert</i>-butyl alcohol at 0℃; for 1h; Stage #2: 5-amino-2-bromo-3-fluorobenzoate methyl ester With triethylamine In tetrahydrofuran; 1,2-dichloro-ethane; <i>tert</i>-butyl alcohol at 30℃; for 24h; 2-3-5 To a solution of 2,4-dichloro-5-(trifluoromethyl)pyrimidine (1.5 g, 6.9 mmol) in a mixture of DCE/t-BuOH ( 54 mL, v/v: 1/1) was added ZnCl2 (8.3 mL, 1N in THF) at 0 oC, the resulting mixture was stirred at 0 oC for 1 h. Then methyl 5-amino-2-bromo-3-fluorobenzoate (1.7 g, 6.9 mmol) and Et3N (766 mg, 7.6 mmol) in DCE/t-BuOH (1:1, 10 mL) were added, the reaction mixture was stirred at 30 oC for 24 h. The mixture was poured into water, and the aqueous phase was extracted with ethyl acetate. The combined organic phase was washed with water, brine, concentrated in vacuo to give a residue, which was purified by silica chromatography (PE/EtOAc (50/1 to 10/1)) to give methyl 2-bromo-5-((4-chloro-5-(trifluoromethyl)pyrimidin-2- yl)amino)-3-fluorobenzoate (1.4 g, yield 47%) as a yellow solid.1H NMR (300 MHz, DMSO-d6) d 11.13 (s, 1H), 8.93 (s, 1H), 8.04 (d, J = 11.2 Hz, 1H), 7.93 (s, 1H), 3.89 (s, 3H) ppm. MS (ESI+): m/z = 425.8, 427.8 (M-H)-
  • 19
  • [ 317-20-4 ]
  • [ 1036389-05-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: sulfuric acid; nitric acid / 1 h / 0 °C 1.2: 0.5 h / 20 °C 2.1: thionyl chloride / 70 °C 3.1: tert.-butylnitrite; copper(I) bromide / acetonitrile / 70 °C 4.1: ammonium chloride; iron / ethanol / 4 h / 80 °C
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