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[ CAS No. 2106-04-9 ] {[proInfo.proName]}

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Chemical Structure| 2106-04-9
Chemical Structure| 2106-04-9
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Product Details of [ 2106-04-9 ]

CAS No. :2106-04-9 MDL No. :MFCD00069415
Formula : C6H5ClFN Boiling Point : -
Linear Structure Formula :- InChI Key :XWBTZHDDWRNOQH-UHFFFAOYSA-N
M.W :145.56 Pubchem ID :75014
Synonyms :

Calculated chemistry of [ 2106-04-9 ]

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 35.81
TPSA : 26.02 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) : -5.79 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.56
Log Po/w (XLOGP3) : 1.97
Log Po/w (WLOGP) : 2.49
Log Po/w (MLOGP) : 2.51
Log Po/w (SILICOS-IT) : 2.21
Consensus Log Po/w : 2.15

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.48
Solubility : 0.485 mg/ml ; 0.00333 mol/l
Class : Soluble
Log S (Ali) : -2.14
Solubility : 1.05 mg/ml ; 0.00721 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.91
Solubility : 0.179 mg/ml ; 0.00123 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.33

Safety of [ 2106-04-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P501-P270-P264-P280-P337+P313-P305+P351+P338-P302+P352-P332+P313-P362-P301+P312+P330 UN#:N/A
Hazard Statements:H302-H315-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 2106-04-9 ]

* 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 [ 2106-04-9 ]
  • Downstream synthetic route of [ 2106-04-9 ]

[ 2106-04-9 ] Synthesis Path-Upstream   1~12

  • 1
  • [ 2106-04-9 ]
  • [ 140-89-6 ]
  • [ 1849-73-6 ]
YieldReaction ConditionsOperation in experiment
87% at 120 - 130℃; Inert atmosphere General procedure: A round-bottomed flask was charged with 2-bromoaniline or 2-fluoro-aniline (>3 g, 1.0 equiv) and potassium O-ethyl carbonodithioate(1.5–1.7 equiv). The mixture was dissolved in DMF (10 volumes) andheated to 120–130 °C until the aniline was fully consumed (3–14 h).The reaction mixture was cooled to r.t. and filtered. The filtrate wasdiluted with H 2 O (50 volumes) and the pH was adjusted to 1–2 usingaqueous 2 M HCl. The solid precipitate was collected, washed withH 2 O and dried to yield the pure product.
Reference: [1] Synthesis (Germany), 2018, vol. 50, # 10, p. 2027 - 2032
  • 2
  • [ 2106-04-9 ]
  • [ 2942-23-6 ]
Reference: [1] Synthesis (Germany), 2018, vol. 50, # 10, p. 2027 - 2032
  • 3
  • [ 2106-04-9 ]
  • [ 2613-22-1 ]
Reference: [1] Journal of the American Chemical Society, 1959, vol. 81, p. 94,95, 97
  • 4
  • [ 2106-49-2 ]
  • [ 2106-04-9 ]
Reference: [1] Journal of the American Chemical Society, 1959, vol. 81, p. 94,95, 97
  • 5
  • [ 3209-22-1 ]
  • [ 2106-04-9 ]
Reference: [1] Journal of the American Chemical Society, 1959, vol. 81, p. 94,95, 97
  • 6
  • [ 2106-04-9 ]
  • [ 351003-48-0 ]
Reference: [1] Journal of Medicinal Chemistry, 2014, vol. 57, # 22, p. 9539 - 9553
  • 7
  • [ 2106-04-9 ]
  • [ 757247-99-7 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 7, p. 1860 - 1864
[2] Patent: WO2011/29392, 2011, A1,
[3] Patent: WO2012/119559, 2012, A1,
  • 8
  • [ 2106-04-9 ]
  • [ 230955-75-6 ]
  • [ 612501-52-7 ]
YieldReaction ConditionsOperation in experiment
95% With hydrogenchloride In acetonitrile for 1 h; Heating / reflux The 4- (3-chloro-2-fluoroanilino)-6-hydroxy-7-methoxyquinazoline starting material used above was prepared as follows: 6-Acetoxy-4-chloro-7-methoxyquinazoline (Example 25-5 in W001/66099 ; 10. 0g, 39.6 mmole) was suspended in acetonitrile (400 ml) and 3-chloro-2-fluoroaniline (6. 05g, 41. 6 mmole) and hydrogen chloride (4. 0M solution in 1,4-dioxane) (10.4 ml, 41.6 mmole) were added. The reaction mixture was refluxed for one hour and then allowed to cool to ambient temperature. The resulting precipitate was filtered off, washed with acetonitrile and diethylether to give a white solid. This solid was added in portions to a stirred 7N methanolic ammonia solution (400 ml). The mixture was stirred for two hours and the precipitate filtered, washed with acetonitrile followed by diethylether and dried under vacuum to give 4- (3-chloro- 2-fluoroanilino) -6-hydroxy-7-methoxyquinazoline as a white solid (12. 1g, 95percent) ; lH NMR Spectrum: (DMSOd6) 3.95 (s, 3H) ; 7.18 (s, lH) ; 7.20-7. 25 (m, 1H); 7.39-7. 44 (m, lH) ; 7.47- 7.52 (m, 11-1) ; 7.65 (s, lH) ; 8.31 (s, 1H) ; 9.45 (br. s, lH) ; Mass Spectrum: (M+H) + 320.
Reference: [1] Patent: WO2003/82831, 2003, A1, . Location in patent: Page/Page column 116
  • 9
  • [ 2106-04-9 ]
  • [ 612501-52-7 ]
Reference: [1] ACS Medicinal Chemistry Letters, 2013, vol. 4, # 8, p. 742 - 746
  • 10
  • [ 1634-04-4 ]
  • [ 2106-04-9 ]
  • [ 144584-65-6 ]
Reference: [1] Patent: US5258526, 1993, A,
  • 11
  • [ 2106-04-9 ]
  • [ 143-33-9 ]
  • [ 873697-68-8 ]
YieldReaction ConditionsOperation in experiment
71% With nickel dibromide In 1-methyl-pyrrolidin-2-one at 195 - 205℃; for 96 h; Example 3; Step 1; A round bottom flask was charged with 1 eq of 3-chloro-2-fluoroaniline (3A), 1-methyl-2-pyrrolidinone (about 1.5 M 3A in NMP), 2.2 eq of sodium cyanide, and 1.35 eq of nickel(II) bromide at RT under N2. The concentration was halved by the introduction of additional NMP under N2 and the solution was gently warmed to 200+/-5° C. and stirred for 4 days under N2. The reaction mixture was allowed to cool to room temperature. The reaction mixture was diluted with 30 volumes of tert-butyl methyl ether (MTBE) and filtered through celite. The celite pad was then rinsed with 10 volumes of MTBE. The organics were washed with 40 volumes of brine, 2.x.40 volumes of water and 40 volumes of brine. The combined organics were dried over sodium sulfate and concentrated to afford a brown solid, which was dried under vacuum (-30 in Hg) at 40° C. for 8 hours to afford the compound of Formula 3B (71percent yield).
71% With nickel dibromide In 1-methyl-pyrrolidin-2-one at 200℃; for 96 h; A round bottom flask was charged with 1 eq of 3-chloro-2-fluoroaniline (3A), 1- methyl-2-pyrrolidinone (about 1.5 M 3 A in NMP), 2.2 eq of sodium cyanide, and 1.35 eq of nickel(II) bromide at RT under N2. The concentration was halved by the introduction of additional NMP under -N2 and the solution was gently warmed to 200+ 5°C and stirred for 4 days under N2. The reaction mixture was allowed to cool to room temperature. The reaction mixture was diluted with 30 volumes of tert-butyl methyl ether (MTBE) and filtered through celite. The celite pad was then rinsed with 10 volumes of MTBE. The organics were washed with 40 volumes of brine, 2 x 40 volumes of water and 40 volumes of brine. The combined organics were dried over sodium sulfate and concentrated to afford a brown solid, which was dried under vacuum (-30 in Hg) at 400C for 8 hours to afford the compound of Formula 3B (71percent yield).
71% With nickel dibromide In 1-methyl-pyrrolidin-2-one at 20 - 205℃; for 96 h; A round bottom flask was charged with 1 eq of 3-chloro-2-fluoroaniline (3A), 1- methyl-2-pyrrolidinone (about 1.5 M 3A in NMP), 2.2 eq of sodium cyanide, and 1.35 eq of nickel(II) bromide at RT under N2. The concentration was halved by the introduction of additional NMP under N2 and the solution was gently warmed to 200+/- 50C and stirred for 4 days under N2. The reaction mixture was allowed to cool to room temperature. The reaction mixture was diluted with 30 volumes of f erf-butyl methyl ether (MTBE) and filtered through celite. The celite pad was then rinsed with 10 volumes of MTBE. The orgam'cs were washed with 40 volumes of brine, 2 x 40 volumes of water and 40 volumes of brine. The combined organics were dried over sodium sulfate and concentrated to afford a brown solid, which was dried under vacuum (-30 in Hg) at 400C for 8 hours to afford the compound of Formula 3B (71 percent yield).
71% With nickel dibromide In 1-methyl-pyrrolidin-2-one at 20 - 205℃; for 96 h; A round bottom flask was charged with 1 eq of 3-chloro-2-fluoroaniline (3A), l-methyl-2-pyrrolidinone (about 1.5 M 3A in NMP), 2.2 eq of sodium cyanide, and 1.35 eq of nickel() bromide at RT under N2. The concentration was halved by die introduction of additional NMP under N2 and the solution was gently warmed to 200+/- 5°C and stirred for 4 days under N2. The reaction mixture was allowed to cool to room temperature. The reaction mixture was diluted with 30 volumes of teft-hutyl methyl ether (MTBE) and filtered through celite. The celite pad was then rinsed with 10 volumes of MTBE. The organics were washed with 40 volumes of brine, 2 x 40 volumes of water and 40 volumes of brine. The combined organics were dried over sodium sulfate and concentrated to afford a brown solid, which was dried under vacuum (~30 in Hg) at 400C for 8 hours to afford the compound of Formula 3B (71percent yield).
71% With nickel dibromide In 1-methyl-pyrrolidin-2-one at 200℃; for 96 h; Example 3 Step 1. A round bottom flask was charged with 1 eq of 3-chloro-2-fluoroaniline (3A), 1- methyl-2-pyrrolidinone (about 1.5 M 3 A in NMP), 2.2 eq of sodium cyanide, and 1.35 eq of nickel(II) bromide at RT under N2. The concentration was halved by the introduction of additional NMP under N2 and the solution was gently warmed to 200+/- 5°C and stirred for 4 days under N2. The reaction mixture was allowed to cool to room temperature. The reaction mixture was diluted with 30 volumes of tert-butyl methyl ether (MTBE) and filtered through celite. The celite pad was then rinsed with 10 volumes of MTBE. The organics were washed with 40 volumes of brine, 2 x 40 volumes of water and 40 volumes of brine. The combined organics were dried over sodium sulfate and concentrated to afford a brown solid, which was dried under vacuum (-30 in Hg) at 400C for 8 hours to afford the compound of Formula 3B (71 percent yield).

Reference: [1] Patent: US2006/14761, 2006, A1, . Location in patent: Page/Page column 32
[2] Patent: WO2007/75377, 2007, A2, . Location in patent: Page/Page column 58
[3] Patent: WO2007/70626, 2007, A2, . Location in patent: Page/Page column 45
[4] Patent: WO2007/70683, 2007, A2, . Location in patent: Page/Page column 88
[5] Patent: WO2007/78839, 2007, A2, . Location in patent: Page/Page column 46
  • 12
  • [ 2106-04-9 ]
  • [ 873697-68-8 ]
YieldReaction ConditionsOperation in experiment
71% With nickel dibromide In 1-methyl-pyrrolidin-2-one at 20 - 205℃; EXAMPLE 3; Step 1 A round bottom flask was charged with 1 eq of 3-chloro-2-fluoroaniline (3A), 1-methyl-2-pyrrolidinone (about 1.5 M 3A in NMP), 2.2 eq of sodium cyanide, and 1.35 eq of nickel(II) bromide at RT under N2. The concentration was halved by the introduction of additional NMP under N2 and the solution was gently warmed to 200+/-5° C. and stirred for 4 days under N2. The reaction mixture was allowed to cool to room temperature. The reaction mixture was diluted with 30 volumes of tert-butyl methyl ether (MTBE) and filtered through celite. The celite pad was then rinsed with 10 volumes of MTBE. The organics were washed with 40 volumes of brine, 2.x.40 volumes of water and 40 volumes of brine. The combined organics were dried over sodium sulfate and concentrated to afford a brown solid, which was dried under vacuum (30 in Hg) at 40° C. for 8 hours to afford the compound of Formula 3B (71percent yield).
Reference: [1] Patent: US2009/192168, 2009, A1, . Location in patent: Page/Page column 19
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