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[ CAS No. 723281-72-9 ] {[proInfo.proName]}

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Chemical Structure| 723281-72-9
Chemical Structure| 723281-72-9
Structure of 723281-72-9 * Storage: {[proInfo.prStorage]}
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Product Details of [ 723281-72-9 ]

CAS No. :723281-72-9 MDL No. :MFCD09909913
Formula : C9H4BrClN2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :KHKPVEMMXJCWGP-UHFFFAOYSA-N
M.W :287.50 Pubchem ID :21984128
Synonyms :

Calculated chemistry of [ 723281-72-9 ]

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 63.28
TPSA : 58.71 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.68 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.82
Log Po/w (XLOGP3) : 3.34
Log Po/w (WLOGP) : 3.56
Log Po/w (MLOGP) : 2.75
Log Po/w (SILICOS-IT) : 1.54
Consensus Log Po/w : 2.6

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.15
Solubility : 0.0202 mg/ml ; 0.0000701 mol/l
Class : Moderately soluble
Log S (Ali) : -4.25
Solubility : 0.0162 mg/ml ; 0.0000562 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -4.54
Solubility : 0.00823 mg/ml ; 0.0000286 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.02

Safety of [ 723281-72-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302+H312+H332-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 723281-72-9 ]

* 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.

  • Upstream synthesis route of [ 723281-72-9 ]
  • Downstream synthetic route of [ 723281-72-9 ]

[ 723281-72-9 ] Synthesis Path-Upstream   1~10

  • 1
  • [ 853908-50-6 ]
  • [ 723281-72-9 ]
YieldReaction ConditionsOperation in experiment
100% for 0.75 h; Reflux 10556] The above reaction scheme illustrates the synthesis of a compound of the invention 2-13. Methylation of starting material 2-1 yields compound 2-2, which is subsequently reduced to the amine 2-3. In a separate reaction, compound 2-4 is converted to a salt, such as an HC1 salt, which is then reacted, for example, with 2-nitrovinyl-hydroxylamine to yield compound 2-6. Further cyclization yields compound 2-7. Halogenation with a reagent such as POd3 results in compound 2-8, which can be coupled with intermediate 2-3 to yield 2-9. The nitro moiety of 2-9 is subsequently reduced to an amine, and a further reaction with 4-nitrophenyl carbonochloridate results in the heterocycle 2-11. The desired compound 2-13 is then prepared by coupling to the benzoxazolyl boronate 2-12, for example in a Suzuki coupling.
93.5% With N-ethyl-N,N-diisopropylamine; trichlorophosphate In acetonitrile at 0 - 75℃; Inert atmosphere 6-Bromo-3-nitroquinolin-4-ol (50 g) and N,N-diisopropylethylamine (60 mL) were added to acetonitrile (500 mL) and stirred for 10 to 15 min under nitrogen atmosphere. The reaction mass was cooled to a temperature of about 0-5 °C and phosphorusoxychloride (50 mL) was added dropwise to the cooled solution while maintaining the temperature below 10°C. The reaction mass was heated to 70 to 75 °C for 2 to 3 h. After completion of the reaction, the mass was cooled to 25 to 30°C. The cooled reaction mass was added dropwise into a mixture of ice-water (1.25 Kg) and sodium chloride (50 g) maintaining the temperature below 0°C. The mixture was stirred for 15 to 30 min. The compound obtained was filtered and washed with ice-cold water (250 mL). The wet compound was dissolved in MDC (750 mL) and filtered through celite bed. The bed was washed with MDC (250 mL). The combined organic layer from the filtrate was separated and washed with ice cold water (500 mL). The separated organic layer was dried over anhydrous sodium sulphate and subjected to distillation below 35°C under vacuum to obtain the title compound (55 g). This compound was dissolved in 500 mL of acetic acid and used for the next step without isolation. Yield: 93.5percent
93% With N-ethyl-N,N-diisopropylamine; trichlorophosphate In acetonitrile at 0 - 100℃; for 2 h; To a solution of 7 (15 g, 0.056 mol) in acetonitrile (80 mL) and DIPEA (15.9 g, 0.123 mol), was added POCI3 (17.1 g, 0.112 mol) dropwisely at O0C. The reaction temperature was slowly raised to 1000C for 2 hours. The mixture was cooled and poured onto ice-water. After Neutralized with aq NaHCC>3, extracted with ethyl acetate, and dried over Na2SO4, the crude product was obtained by evaporating of solution to dryness (15 g, 93percent) as a brown solid. MS (m/z) (M++H): 287, 289.
91.1% With trichlorophosphate In N,N-dimethyl-formamide at 110℃; Compound 4a (19.5 g, 0.072 mol)Add to a three-necked flask containing phosphorus oxychloride (212 ml, 2.174 mol).Add 6 drops of DMF,Warm up to 110 ° C,Reflux for 0.2-3h.TLC detection [V (petroleum ether): V (ethyl acetate) = 1 : 1]Shows that the reaction is complete,The reaction liquid is distilled under reduced pressure to obtain a yellowish viscous material.Add ice saturated sodium bicarbonate solution (500 ml),Stir for 1h,Filtering,The filter residue was washed with water (20 mL).Extracted three times with ethyl acetate (30 mL×3).The extract was Concentrate the extract to dry riceyellowSolid 19.0g,The yield is 91.1percent
68% for 1.5 h; Reflux After a suspension of 3g (10 mmol) in phosphorus oxychloride (15 mL) was added triethylamine slowly. The mixture was stirred and refluxed for 1.5 h. The phosphorus oxychloride was quenched with water carefully, then the suspension was filtered and the decolorized solid was recrystallized with ethyl acetate and petroleum ether. Yield 68percent. HPLC purity: 98.8percent.
53% at 120℃; for 1 h; [0074] 26.8 g (99 mmol) of Intermediate 2 was placed in a 500-ml single-necked flask, added with 200 ml of phosphorusoxychloride, and refluxed at 120°C for 1 h. The reaction was monitored by TLC. After the reaction was completed, thereaction mixture was poured into a large amount of ice water and stirred, leading to formation of precipitates. The reactionmixture was filtered, and the filter cake was washed with ice water, and then dissolved in methylene chloride. The organicphase was washed with brine three times, dried by anhydrous magnesium sulfate, and rotary evaporated to dryness toafford 16.1 g of Intermediate 3. Yield: 53percent.
53% at 120℃; for 1 h; 26.8 g (99 mmol) of Intermediate 2 was placed in a 500 ml single-neck flask,200 ml of phosphorus oxychloride was added thereto,120 ° C under the return of lh,TLC monitoring. After completion of the reaction, it was poured into a large amount of ice water and stirred to precipitate. The filter cake was washed with ice water and dissolved in methylene chloride. The organic phase was washed three times with brine, dried over anhydrous magnesium sulphate, and dried to give intermediate 3 16.1 g, 53percent
38% at 120℃; for 0.75 h; 6-Bromo-3-nitroquinolin-4-ol (Compound of step 2, 20 g, 74.3 mmol) and POCI3 (150 mL, 1613 mmol) were stirred for 45 minutes at 120 0C. The mixture was cooled to RT and poured slowly into ice-water. The precipitate was filtered, washed with ice-cold water, and dissolved in CH2CI2. The organic layer was washed with cold brine, and was dried over Na2SOzJ. The solvent was evaporated to dryness to obtain the title compound.Yield: 8 g (38 percent); 1H NMR (CDCl3, 500 MHz): δ 9.275 (s, IH), 8.611-8.615 (d, IH, J= 2Hz), 8.100- 8.118 (d, IH, J=9Hz), 8.026-8.048 (dd, IH, J= 8.5Hz, 2Hz).
38% at 120℃; for 0.75 h; Step 3:
6-Bromo-4-chloro-3-nitroquinoline
6-Bromo-3-nitroquinolin-4-ol (Compound of step 2, 20 g, 74.3 mmol) and POCl3 (150 mL, 1613 mmol) were stirred for 45 minutes at 120° C.
The mixture was cooled to RT and poured slowly into ice-water.
The precipitate was filtered, washed with ice-cold water, and dissolved in CH2Cl2.
The organic layer was washed with cold brine, and was dried over Na2SO4.
The solvent was evaporated to dryness to obtain the title compound.
Yield: 8 g (38percent); 1H NMR (CDCl3, 500 MHz): δ 9.275 (s, 1H), 8.611-8.615 (d, 1H, J=2 Hz), 8.100-8.118 (d, 1H, J=9 Hz), 8.026-8.048 (dd, 1H, J=8.5 Hz, 2 Hz).

Reference: [1] Patent: US2015/320727, 2015, A1, . Location in patent: Paragraph 0555; 0556
[2] Patent: WO2015/145369, 2015, A1, . Location in patent: Page/Page column 38
[3] Patent: WO2009/155527, 2009, A2, . Location in patent: Page/Page column 142
[4] MedChemComm, 2016, vol. 7, # 2, p. 297 - 310
[5] Patent: CN108456165, 2018, A, . Location in patent: Paragraph 0047; 0081-0082
[6] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 3, p. 799 - 807
[7] Patent: EP3072893, 2016, A1, . Location in patent: Paragraph 0071; 0074
[8] Patent: CN104411706, 2016, B, . Location in patent: Paragraph 0197-0198
[9] Archiv der Pharmazie, 2018, vol. 351, # 6,
[10] Patent: WO2011/1212, 2011, A1, . Location in patent: Page/Page column 38
[11] Patent: US2012/108627, 2012, A1, . Location in patent: Page/Page column 15-16
[12] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 3, p. 1027 - 1030
[13] Patent: WO2005/54237, 2005, A1, . Location in patent: Page/Page column 53-54
[14] Patent: WO2005/54238, 2005, A1, . Location in patent: Page/Page column 63
[15] Patent: WO2008/64093, 2008, A2, . Location in patent: Page/Page column 17
[16] Patent: WO2007/75468, 2007, A1, . Location in patent: Page/Page column 71
[17] Patent: WO2010/139731, 2010, A1, . Location in patent: Page/Page column 94
[18] Patent: WO2012/7926, 2012, A1, . Location in patent: Page/Page column 47
[19] Patent: WO2012/77031, 2012, A1, . Location in patent: Page/Page column 42-43
[20] Patent: WO2012/116237, 2012, A2, . Location in patent: Page/Page column 119
[21] Patent: WO2013/23119, 2013, A1, . Location in patent: Page/Page column 27
[22] Patent: WO2014/141118, 2014, A1, . Location in patent: Page/Page column 45
[23] Patent: WO2014/151147, 2014, A1, . Location in patent: Paragraph 00641
[24] Patent: US2015/30588, 2015, A1, . Location in patent: Page/Page column 74
[25] Patent: US9295673, 2016, B2, . Location in patent: Page/Page column 360
[26] Patent: US9358229, 2016, B2, . Location in patent: Page/Page column 18
[27] Journal of Medicinal Chemistry, 2017, vol. 60, # 14, p. 6337 - 6352
[28] Molecules, 2018, vol. 23, # 7,
[29] Patent: CN108503634, 2018, A, . Location in patent: Paragraph 0274; 0275; 0280; 0281
[30] Patent: WO2006/122806, 2006, A2, . Location in patent: Page/Page column 48
[31] Patent: WO2010/139747, 2010, A1, . Location in patent: Page/Page column 78
  • 2
  • [ 145369-94-4 ]
  • [ 723281-72-9 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 3, p. 799 - 807
[2] Molecules, 2018, vol. 23, # 7,
[3] Archiv der Pharmazie, 2018, vol. 351, # 6,
[4] Patent: CN108456165, 2018, A,
  • 3
  • [ 1201643-75-5 ]
  • [ 723281-72-9 ]
Reference: [1] Patent: WO2011/1212, 2011, A1,
[2] MedChemComm, 2016, vol. 7, # 2, p. 297 - 310
[3] Journal of Medicinal Chemistry, 2017, vol. 60, # 14, p. 6337 - 6352
[4] Patent: CN108503634, 2018, A,
[5] Patent: WO2006/122806, 2006, A2,
[6] Patent: WO2009/155527, 2009, A2,
  • 4
  • [ 5794-88-7 ]
  • [ 723281-72-9 ]
Reference: [1] Patent: WO2012/116237, 2012, A2,
[2] Patent: WO2014/151147, 2014, A1,
[3] Patent: US2015/320727, 2015, A1,
[4] MedChemComm, 2016, vol. 7, # 2, p. 297 - 310
[5] Patent: US9295673, 2016, B2,
[6] Patent: WO2006/122806, 2006, A2,
[7] Patent: WO2009/155527, 2009, A2,
  • 5
  • [ 74189-16-5 ]
  • [ 723281-72-9 ]
Reference: [1] Patent: WO2012/116237, 2012, A2,
[2] Patent: WO2014/151147, 2014, A1,
[3] Patent: US9295673, 2016, B2,
[4] Patent: US2015/30588, 2015, A1,
[5] Patent: US2015/320727, 2015, A1,
[6] Patent: WO2006/122806, 2006, A2,
  • 6
  • [ 187278-01-9 ]
  • [ 723281-72-9 ]
Reference: [1] Molecules, 2018, vol. 23, # 7,
[2] Archiv der Pharmazie, 2018, vol. 351, # 6,
[3] Patent: CN108456165, 2018, A,
  • 7
  • [ 106-40-1 ]
  • [ 723281-72-9 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 3, p. 799 - 807
[2] Molecules, 2018, vol. 23, # 7,
  • 8
  • [ 853908-49-3 ]
  • [ 723281-72-9 ]
Reference: [1] Patent: US2012/108627, 2012, A1,
[2] Patent: WO2012/77031, 2012, A1,
[3] Patent: WO2012/116237, 2012, A2,
[4] Patent: WO2013/23119, 2013, A1,
[5] Patent: WO2014/151147, 2014, A1,
[6] Patent: US9295673, 2016, B2,
[7] Patent: US2015/30588, 2015, A1,
[8] Patent: EP3072893, 2016, A1,
[9] Patent: US9358229, 2016, B2,
[10] Patent: CN104411706, 2016, B,
[11] Patent: WO2012/7926, 2012, A1,
  • 9
  • [ 1551219-53-4 ]
  • [ 723281-72-9 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 3, p. 799 - 807
  • 10
  • [ 118-92-3 ]
  • [ 723281-72-9 ]
Reference: [1] MedChemComm, 2016, vol. 7, # 2, p. 297 - 310
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