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[ CAS No. 1810-66-8 ] {[proInfo.proName]}

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Chemical Structure| 1810-66-8
Chemical Structure| 1810-66-8
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Product Details of [ 1810-66-8 ]

CAS No. :1810-66-8 MDL No. :MFCD08703169
Formula : C9H6BrNO Boiling Point : -
Linear Structure Formula :- InChI Key :YLAFBGATSQRSTB-UHFFFAOYSA-N
M.W : 224.05 Pubchem ID :12378943
Synonyms :

Calculated chemistry of [ 1810-66-8 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 52.27
TPSA : 32.86 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) : -6.28 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.92
Log Po/w (XLOGP3) : 1.95
Log Po/w (WLOGP) : 2.29
Log Po/w (MLOGP) : 2.37
Log Po/w (SILICOS-IT) : 3.26
Consensus Log Po/w : 2.36

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.07
Solubility : 0.189 mg/ml ; 0.000843 mol/l
Class : Soluble
Log S (Ali) : -2.26
Solubility : 1.22 mg/ml ; 0.00544 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.47
Solubility : 0.00764 mg/ml ; 0.0000341 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.51

Safety of [ 1810-66-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338-P310 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1810-66-8 ]

* 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 [ 1810-66-8 ]
  • Downstream synthetic route of [ 1810-66-8 ]

[ 1810-66-8 ] Synthesis Path-Upstream   1~17

  • 1
  • [ 1810-66-8 ]
  • [ 1810-71-5 ]
YieldReaction ConditionsOperation in experiment
92% at 100℃; for 15 h; Step 1 : A stirred solution of 6-bromoquinolin-2(1 /-/)-one (1.0 g, 4.4 mmol, 1.0 equiv) in phosphorous oxychloride (15 mL) was heated to 100°C for 15 h. The solvent was completely evaporated and water was added to the residue. The precipitated solid was filtered and dried under vacuum to obtain 6-bromo-2-chloroquinoline (1.0 g, 92 percent) as pink solid. LCMS (ES) m/z = 241.0, 243.0 [M+H]+. H NMR (400 MHz, DMSO-d6) δ ppm 7.41 (d, J = 8.4 Hz, 1 H), 7.79 - 7.82 (m, 1 H), 7.89 (d, J = 9.2 Hz, 1 H), 7.98 - 7.99 (m, 1 H), 8.02 (d, J = 8.8 Hz, 1 H).
85%
Stage #1: for 1 h; Heating / reflux
6-Bromo-2-chloroquinoline. The solution of the compound from Example 6 b)(3.Og, 13 mmol) in POCI3 (25 ml_) was refluxed for an hour. The mixture was cooled to the ambient temperature and quenched with ice water. The precipitate was filtered, washed with water and dried in vacuo to afford the title compound as a yellow solid. (2.7 g, 85percent). 1 H NMR (400 MHz, CHLOROFORM-of) δ ppm 8.06 (d, J=8.34 Hz, 1 H) 8.02 (d, J=2.02 Hz, 1 H) 7.93 (d, J=9.09 Hz, 1 H) 7.84(dd, J=9.09, 2.27 Hz, 1 H) 7.44 (d, J=8.59 Hz, 1 H).
80% for 1 h; Heating / reflux Part C. Preparation of 6-bromo-2-chloroquinoline.; [00795] To phosphorus oxychloride (2.5ml, 26.8mmol) was added, in portions, the product from Part B(200mg, 0.893mmol). Refluxed for Ih, cooled to room temperature and poured onto crushed ice.Extracted with CHCl3, extracts combined, dried overmgSO4, filtered and concentrated under vacuum to give the title compound (173mg, 80percent).
80% for 1 h; Heating / reflux [00537] Part C. Preparation of -bromo-^-chloroquinoline.; [00538] To phosphorus oxychloride (2.5ml, 26.8mmol) was added, in portions, the product from Part B(200mg, 0.893mmol). Refluxed for Ih, cooled to room temperature and poured onto crushed ice.Extracted with CHCI3, extracts combined, dried overmgSO,), filtered and concentrated under vacuum to give the title compound (173mg, 80percent).
67% at 60 - 100℃; Example A4; a. Preparation of intermediate 5; A mixture of 6-bromo-2 (lH)-quinolinone (0.089 mol) in POC13 (55 ml) was stirred at 60°C overnight, then at 100°C for 3 hours and the solvent was evaporated. The residue was taken up in CH2Cl2, poured out into ice water, basified with NHaOH concentrated, filtered over celite and extracted with CH2C12. The organic layer was separated, dried (MgSO4), filtered and the solvent was evaporated. Yield: 14. 5g of intermediate 5 (67percent).
67%
Stage #1: at 60 - 100℃;
Stage #2: With ammonia In dichloromethane; water at 0℃;
A mixture of 6-bromo-2(7H)-quinolinone (0.089 mol) in POCl3 (55 ml) was stirred at 60°C overnight, then at 100°C for 3 hours and the solvent was evaporated. The residue EPO <DP n="39"/>was taken up in CH2CI2, poured out into ice water, basified with NH4OH concentrated, filtered over celite and extracted with CH2CI2. The organic layer was separated, dried(MgSO4), filtered and the solvent was evaporated. Yield: 14.5g of intermediate 5(67percent).

Reference: [1] Patent: WO2017/46739, 2017, A1, . Location in patent: Page/Page column 78
[2] Journal of the American Chemical Society, 2016, vol. 138, # 25, p. 7808 - 7811
[3] Patent: WO2006/132739, 2006, A2, . Location in patent: Page/Page column 36
[4] European Journal of Medicinal Chemistry, 2000, vol. 35, # 10, p. 931 - 940
[5] Patent: WO2009/39127, 2009, A1, . Location in patent: Page/Page column 181
[6] Patent: WO2009/39134, 2009, A1, . Location in patent: Page/Page column 110
[7] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 22, p. 5907 - 5912
[8] Patent: WO2005/75428, 2005, A1, . Location in patent: Page/Page column 31-32
[9] Patent: WO2007/14941, 2007, A2, . Location in patent: Page/Page column 36-37
[10] Journal of Medicinal Chemistry, 1988, vol. 31, # 10, p. 2048 - 2056
[11] Bioorganic and Medicinal Chemistry Letters, 1999, vol. 9, # 18, p. 2753 - 2758
[12] Patent: WO2004/24731, 2004, A1, . Location in patent: Page 50
[13] Chemical and Pharmaceutical Bulletin, 2014, vol. 62, # 6, p. 508 - 518
[14] Patent: WO2015/96035, 2015, A1, . Location in patent: Page/Page column 53; 54
[15] Patent: WO2015/100147, 2015, A1, . Location in patent: Page/Page column 54
  • 2
  • [ 1810-66-8 ]
  • [ 1810-71-5 ]
Reference: [1] Journal of Medicinal Chemistry, 2011, vol. 54, # 16, p. 5836 - 5857
  • 3
  • [ 327058-51-5 ]
  • [ 1810-66-8 ]
YieldReaction ConditionsOperation in experiment
97% at 100℃; 6-Bromo-2(1 /-/)-quinolinone. The solution of the compound from Example 6 a) (6.0 g, 22.2 mmol) in concentrated H2SO4 (30 mL) was heated in 100 0C EPO <DP n="37"/>overnight. The mixture was cooled to ambient temperature and quenched with ice water. The precipitate was filtered, washed with water and dried in vacuo to afford the title compound as a white solid (4.8 g, 97percent). MS(ES+) m/e 225 [M+H]+.
89% at 0 - 20℃; for 3 h; Inert atmosphere Sulfuric acid (29.0 mL, 544 mmol) was added to (E)-N-(4-bromophenyl)-3-ethoxyacrylamide (11.2 g, 45.9 mmol) at 0°C under N2 (g). The mixture was stirred for 3 h at room temperature. The reaction was quenched by transferring the reaction mixture to ice fragments. At this point, the color of the reaction mixture turned to pink. After the ice melted, the quenched mixture was filtered and washed with sufficient H2O to afford bromoquinoline 6 (9.10 g, 89 percent) as a pink solid:
Reference: [1] Patent: WO2006/132739, 2006, A2, . Location in patent: Page/Page column 35-36
[2] Chemical and Pharmaceutical Bulletin, 2014, vol. 62, # 6, p. 508 - 518
[3] European Journal of Medicinal Chemistry, 2000, vol. 35, # 10, p. 931 - 940
[4] Journal of Medicinal Chemistry, 2005, vol. 48, # 1, p. 306 - 311
  • 4
  • [ 106-40-1 ]
  • [ 1810-66-8 ]
Reference: [1] European Journal of Medicinal Chemistry, 2000, vol. 35, # 10, p. 931 - 940
[2] Patent: US6534535, 2003, B1,
[3] Patent: WO2013/166013, 2013, A1,
[4] Organic Process Research and Development, 2017, vol. 21, # 7, p. 1003 - 1011
[5] Patent: WO2006/132739, 2006, A2,
  • 5
  • [ 54934-81-5 ]
  • [ 1810-66-8 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 1999, vol. 9, # 18, p. 2753 - 2758
[2] Patent: WO2013/166013, 2013, A1, . Location in patent: Paragraph 0109; 0110
[3] Chemical Communications, 2014, vol. 50, # 25, p. 3359 - 3362
  • 6
  • [ 1132940-92-1 ]
  • [ 1810-66-8 ]
YieldReaction ConditionsOperation in experiment
59% at 20℃; for 3 h; Part B. Preparation of 6-Bromoquinolin-2( 1 H)-one.; [00793] The product from Part A (395mg, 1.542mmol) was added in portions to H2SO4 (4.5ml). Stirred for 3h at room temperature, poured onto crushed ice. Solid filtered, washed with water and dried under vacuum to give the title compound (203 mg, 59 percent).
59% at 20℃; for 3 h; [00535] Part B. Preparation of 6-Bromoquinolin-2(lH)-one.; [00536] The product from Part A (395mg, 1.542mmol) was added in portions to H2SO4 (4.5ml). Stirred for 3h at room temperature, poured onto crushed ice. Solid filtered, washed with water and dried under vacuum to give the title compound (203 mg, 59 percent).
Reference: [1] Patent: WO2009/39127, 2009, A1, . Location in patent: Page/Page column 181
[2] Patent: WO2009/39134, 2009, A1, . Location in patent: Page/Page column 110
  • 7
  • [ 577967-86-3 ]
  • [ 1810-66-8 ]
YieldReaction ConditionsOperation in experiment
64% at 0 - 20℃; for 4.25 h; To a mixture of ethyl 3,3-diethoxypropionate (62 g, 326 mmol) and water (100 ml) was added NaOH (16.0 g) while stirring. Stirring at 110° C. (open flask). After 40 min the mixture was homogeneous, heating was interrupted, and the mixture was allowed to cool to room temperature. The mixture was acidified (approx 35 ml conc. HCl, pH 3-2) and extracted (4.x.dichloromethane). The combined extracts were washed with brine (1.x.50 ml), dried (magnesium sulfate), and concentrated. 48 g of an oil was obtained. [0850] To the oil was dropwise added thionyl chloride (80 ml). The mixture was stirred at reflux (80° C.) for 1 h 30 min. After careful concentration the residue weighted 48 g (theoretical wheight should be 43 g). The acid chloride was kept overnight at -20° C. [0851] This product is mixed with dichloromethane (70 ml) and 5/7 of this solution (approx 230 mmol) was added to a solution of 4-bromoaniline (34.5 g, 201 mmol) and pyridine (50 ml) in dichloromethane (150 ml), and the mixture was shaken at room temperature over night. The mixture was filtered, and the resulting solid was washed with dichloromethane, and dried, to yield 21 g of N-(4-bromophenyl)-3-ethoxyacrylamide as colorless solid. To the filtrate was added a mixture of water (700 ml) and concentrated hydrochloric acid (50 ml). A solid precipitated upon shaking, and was filtered off, washed with dichloromethane and AcOEt, and dried. Additional 14.4 g of product were obtained. [0852] The filtrates were extracted (3.x.dichloromethane), washed once with brine, dried, and concentrated. Additional 18 g of product resulted. Total yield: 53.4 g. [0853] This product (58.8 g; 218 mmol) was mixed with ice-cold concentrated sulfuric acid (390 ml) and the mixture was stirred first at 0° C. for 15 min (until almost all acrylamide had dissolved) and then at room temperature for 4 h. The mixture was then poured into ice water (3 l) and allowed to stand overnight. The mixture was filtered, and the solid was washed with water. The solid was transferred into a flask with the aid of acetonitrile, ethanol, and dichloromethane, and the suspension was concentrated under reduced pressure. The residue was resuspended in acetonitrile (300 ml), heated to reflux, and allowed to stand at room temperature overnight. Filtration and drying of the solid under reduced pressure yielded 31.3 g (64percent) of 6-bromo-2-quinolone as a yellow solid. [0854] This quinolone (6.28 g, 28.0 mmol) was mixed with copper(I) cyanide (5.02 g, 56.1 mmol) and NMP (15 ml), and the mixture was stirred under reflux (202° C.) for 6 h, and then at room temperature overnight. Water (150 ml) was added, the mixture was filtered, and the solid was washed with water. The solid was resuspended in 1 N hydrochloric acid (200 ml) and iron(III) chloride hexahydrate (17.8 g) was added. The resulting mixture was stirred at room temperature for 3 d, filtered, and the solid was washed once with water, stripped with ethanol, and dried under reduced pressure, to yield 4.33 g (91percent) of 6-cyano-2-quinolone as a gray solid. Treatment of the product with POCl3 and then with 1-isopropylpiperazine as described in the General Procedure (B) yielded the title compound. [0855] 1H NMR (DMSO-d6) δ1.31 (d, J=7 Hz, 6H), 3.10 (m, 2H), 3.52 (m, 5H), 4.79 (m, 2H), 7.49 (d, J=8 Hz, 1H), 7.71 (d, J=8 Hz, 1H), 7.86 (d, J=8 Hz, 1H), 8.23 (d, J=8 Hz, 1H), 8.35 (s, 1H), 10.73 (br s, 1H); HPLC-MS: m/z 281 (MH+); Rt=1.62 min.
Reference: [1] Patent: US2003/236259, 2003, A1, . Location in patent: Page 54
  • 8
  • [ 106-40-1 ]
  • [ 140-88-5 ]
  • [ 1810-66-8 ]
Reference: [1] Organic Letters, 2015, vol. 17, # 2, p. 222 - 225
  • 9
  • [ 1035669-79-4 ]
  • [ 1810-66-8 ]
Reference: [1] Tetrahedron Letters, 2008, vol. 49, # 22, p. 3677 - 3681
  • 10
  • [ 914918-89-1 ]
  • [ 1810-66-8 ]
Reference: [1] Patent: WO2006/122154, 2006, A2, . Location in patent: Page/Page column 65-66
  • 11
  • [ 71205-21-5 ]
  • [ 1810-66-8 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 22, p. 5907 - 5912
[2] Synthesis, 2008, # 13, p. 2039 - 2044
  • 12
  • [ 5332-25-2 ]
  • [ 1810-66-8 ]
Reference: [1] Green Chemistry, 2018, vol. 20, # 3, p. 760 - 764
  • 13
  • [ 7664-93-9 ]
  • [ 327058-51-5 ]
  • [ 1810-66-8 ]
Reference: [1] Patent: US2004/209865, 2004, A1,
  • 14
  • [ 66416-72-6 ]
  • [ 1810-66-8 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 22, p. 5907 - 5912
  • 15
  • [ 99455-05-7 ]
  • [ 1810-66-8 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1993, # 2, p. 181 - 184
  • 16
  • [ 6931-16-4 ]
  • [ 1810-66-8 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1993, # 2, p. 181 - 184
  • 17
  • [ 1810-66-8 ]
  • [ 791626-59-0 ]
Reference: [1] Patent: WO2006/132739, 2006, A2,
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