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Chemical Structure| 13669-42-6
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Product Details of [ 13669-42-6 ]

CAS No. :13669-42-6 MDL No. :MFCD00006768
Formula : C10H7NO Boiling Point : -
Linear Structure Formula :- InChI Key :RYGIHSLRMNXWCN-UHFFFAOYSA-N
M.W : 157.17 Pubchem ID :83641
Synonyms :

Calculated chemistry of [ 13669-42-6 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 47.13
TPSA : 29.96 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) : -6.0 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.43
Log Po/w (XLOGP3) : 1.77
Log Po/w (WLOGP) : 2.05
Log Po/w (MLOGP) : 1.14
Log Po/w (SILICOS-IT) : 2.62
Consensus Log Po/w : 1.8

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.48
Solubility : 0.52 mg/ml ; 0.00331 mol/l
Class : Soluble
Log S (Ali) : -2.02
Solubility : 1.51 mg/ml ; 0.00961 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.63
Solubility : 0.0364 mg/ml ; 0.000232 mol/l
Class : Soluble

Medicinal Chemistry

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

Safety of [ 13669-42-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261 UN#:N/A
Hazard Statements:H315-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 13669-42-6 ]

* 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 [ 13669-42-6 ]
  • Downstream synthetic route of [ 13669-42-6 ]

[ 13669-42-6 ] Synthesis Path-Upstream   1~19

  • 1
  • [ 67-56-1 ]
  • [ 13669-42-6 ]
  • [ 53951-84-1 ]
Reference: [1] Organic Letters, 2018, vol. 20, # 17, p. 5172 - 5176
  • 2
  • [ 5332-24-1 ]
  • [ 68-12-2 ]
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YieldReaction ConditionsOperation in experiment
45% With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.166667 h; General procedure: To a solution of 13a (100mg, 0.48mmol) in dry THF (1.5mL) at -78°C nBuLi (2.5M in n-hexane, 300μL, 0.72mmol) was added dropwise.
The resulting solution turned to red and DMF (192μL, 2.49mmol) was added.
After 10minat -78°C the mixture was quenched with water.
The reaction was poured into a saturated aqueous solution of NaHCO3 (10mL) and extracted with EtOAc (3*10mL).
The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated.
The residue was purified by flash chromatography on silica gel (10percent EtOAc in n-hexane) to afford the title compound as a yellow solid (53percent yield).
Reference: [1] Tetrahedron Letters, 2003, vol. 44, # 10, p. 2033 - 2035
[2] Tetrahedron, 2003, vol. 59, # 43, p. 8629 - 8640
[3] Tetrahedron, 2002, vol. 58, # 17, p. 3387 - 3400
[4] European Journal of Medicinal Chemistry, 2019, p. 290 - 320
  • 3
  • [ 6480-68-8 ]
  • [ 13669-42-6 ]
Reference: [1] Advanced Synthesis and Catalysis, 2010, vol. 352, # 13, p. 2166 - 2170
[2] Journal of Organic Chemistry, 1999, vol. 64, # 6, p. 1823 - 1830
[3] Patent: WO2012/178015, 2012, A2,
  • 4
  • [ 215189-85-8 ]
  • [ 13669-42-6 ]
Reference: [1] Patent: WO2012/178015, 2012, A2, . Location in patent: Page/Page column 114-115
  • 5
  • [ 5332-24-1 ]
  • [ 119072-55-8 ]
  • [ 13669-42-6 ]
Reference: [1] Organic Letters, 2014, vol. 16, # 13, p. 3492 - 3495
  • 6
  • [ 33816-43-2 ]
  • [ 13669-42-6 ]
Reference: [1] Chemical Communications, 2015, vol. 51, # 32, p. 7035 - 7038
  • 7
  • [ 5332-24-1 ]
  • [ 50978-45-5 ]
  • [ 13669-42-6 ]
Reference: [1] Angewandte Chemie - International Edition, 2013, vol. 52, # 33, p. 8611 - 8615[2] Angew. Chem., 2013, vol. 125, # 33, p. 8773 - 8777,5
  • 8
  • [ 5332-24-1 ]
  • [ 20461-86-3 ]
  • [ 13669-42-6 ]
Reference: [1] Angewandte Chemie - International Edition, 2017, vol. 56, # 6, p. 1500 - 1505[2] Angew. Chem., 2017, vol. 129, # 6, p. 1522 - 1527,6
  • 9
  • [ 25283-63-0 ]
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Reference: [1] Helvetica Chimica Acta, 2018, vol. 101, # 5,
  • 10
  • [ 34846-64-5 ]
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Reference: [1] Bulletin of the Polish Academy of Sciences, Chemistry, 1986, vol. 34, # 7-8, p. 281 - 287
[2] Archives of Biochemistry, 1951, vol. 31, p. 190,191
  • 11
  • [ 5332-24-1 ]
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Reference: [1] Bulletin of the Polish Academy of Sciences, Chemistry, 1986, vol. 34, # 7-8, p. 281 - 287
[2] RSC Advances, 2015, vol. 5, # 22, p. 17060 - 17063
  • 12
  • [ 612-58-8 ]
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Reference: [1] Journal of the Chemical Society, 1951, p. 1145,1147
[2] Liebigs Annalen der Chemie, 1988, p. 455 - 464
[3] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 14, p. 3771 - 3774
  • 13
  • [ 62-53-3 ]
  • [ 13669-42-6 ]
  • [ 135304-93-7 ]
Reference: [1] Synthesis, 2001, # 9, p. 1351 - 1355
  • 14
  • [ 406192-08-3 ]
  • [ 13669-42-6 ]
Reference: [1] Journal of the Chemical Society, 1943, p. 413,416
  • 15
  • [ 59282-61-0 ]
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Reference: [1] Journal of the Chemical Society, 1943, p. 413,416
  • 16
  • [ 50741-46-3 ]
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Reference: [1] Journal of the Chemical Society, 1943, p. 413,416
  • 17
  • [ 13669-42-6 ]
  • [ 13669-51-7 ]
YieldReaction ConditionsOperation in experiment
90%
Stage #1: With sodium tetrahydroborate In methanol for 0.333333 h;
Stage #2: With water In methanol
Example 15 2-(2,6-Dioxo-piperidin-3-yl)-4-(quinolin-3-ylmethoxy)-isoindole-l,3-dioneStep 1:[203] 3-Quinolinecarbaldehyde (2.00 g, 12.7 mmol) was dissolved in 25 mL of methanol. To this solution was added sodium borohydride (0.24 g, 6.4 mmol) in small portions over a period of 20 minutes. Then 2 mL of water were added and the mixture was evaporated. The residue was dissolved in ethyl acetate (75 mL) and washed with water (3 x 75 mL), dried (MgSO4) and evaporated, providing 1.8 g of quinolin-3-yl-methanol in 90percent yield; 1H NMR (DMSO-J6) δ 4.89 (s, 2H), 7.53 (t, J = 7.1 Hz, IH), 7.64-7.71 (m, IH), 7.77 (d, J = 8.2 Hz, IH), 8.04-8.12 (m, 2H), 8.83 (d, J = 2.0 Hz, IH).
86%
Stage #1: With sodium tetrahydroborate In methanol at 20℃; for 3 h;
Stage #2: With water; ammonium chloride In methanol
Example 112; 5-(Quinolin-3-ylmethoxy)-quinazoline-2,4-diamine; [00324] Step 1; Sodium borohydride (240 mg, 6.4 mmol) was added in portions to a solution of 3-Quinoline-carboxaldehyde (910 mg, 5.8 mmol) in methanol at room temperature. Reaction was quenched after 3 hours stirring with 10 mls (aq) sat. NH4Cl. Mixture was extracted with ethyl acetate (3 X 30 ml). Combined organics were washed with brine and dried over MgS04. Crude Quinolin-3-ylmethanol was obtained upon filtration and concentration (795 mg; 86 percent yield).
71% at 0 - 20℃; Quinolin-3-ylmethanol MDE 32002
To a solution of 3-quinolinecarboxaldehyde (0.39 g, 2.48 mmol) in absolute EtOH (25 mL) at 0° C. in a 100 mL round-bottomed flask equipped with a magnetic stirrer was added NaBH4 (48 mg, 1.26 mmol) and the mixture was stirred overnight at RT. Then a second portion of NaBH4 (48 mg, 1.26 mmol) was added at RT and stirring was continued for 1 h at RT.
The solution was then cooled down to 0° C. before quenching with a 6 N aq. HCl solution (2 mL).
The reaction mixture was stirred at RT for 15 min and then basified with a 2 N aq. NaOH solution (8 mL).
EtOH was removed at 40° C. under vacuum and the residue was extracted with CH2Cl2 (2*50 mL).
The organic phase was washed with brine (10 mL), dried over Na2SO4, filtered and concentrated at 40° C. under vacuum.
Purification by column chromatography (SiO2, eluent cyclohexane:EtOAc=100:0 to 0:100) gave, after evaporation and drying, quinolin-3-ylmethanol MDE 32002 as an off-white solid (280 mg, 71percent yield).
MW: 159.19; Yield: 71percent; Off-white solid; Mp (° C.): 87.6
Rf: 0.25 (EtOAc=100percent).
1H-NMR (CDCl3, δ): 3.80 (broad s, 1H, OH), 4.90 (s, 2H, OCH2), 7.49-7.54 (m, 1H, ArH), 7.64-7.70 (m, 1H, ArH), 7.76 (d, 1H, J=8.1 Hz, ArH), 8.50 (d, 1H, J=8.5 Hz, ArH), 8.15 (s, 1H, ArH), 8.80 (s, 1H, ArH).
13C-NMR (CDCl3, δ): 62.6, 126.9, 127.7, 127.9, 128.9, 129.4, 133.8, 147.3, 150.1 (1*C not observed).
MS-ESI m/z (percent rel. Int.): 160 ([MH]+, 100).
79.5% With sodium borohydrid In methanol; chloroform; sodium hydrogencarbonate; ethyl acetate EXAMPLE 10
Preparation of 3-Quinolinemethanol
To a solution of 3.14 g (20 mmol) of 3-quinolinecarboxaldehyde in 60 mL of methanol was added portionwise 0.95 g (25 mmol) of sodium borohydride at 0° C.
The reaction mixture was then stirred at room temperature for 2 hours.
Excess sodium borohydride was quenched with acetic acid and the reaction mixture was evaporated in vacuo.
The residue was dissolved in dilute aqueous sodium bicarbonate and extracted three times with ethyl acetate.
The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and evaporated in vacuo to give an oil.
The oil was chromatographed on silica gel, using first 3:2 chloroform/ethyl acetate and then ethyl acetate as eluents, to afford 2.35 g (79.5percent) of the title compound of the structural formula STR82 The product was characterized as follows: TLC Rf =0.30 (ethyl acetate); IR (neat) ν 3120, 1580, 1500, 1060 cm-1; NMR (CDCl3) δ 8.73 (1H, d, J=2 Hz), 8.07 (1H, s), 8.02 (1H, d, J=7 Hz), 7.8-7.3 (3H, m), 4.82 (2H, s).

Reference: [1] Journal of Organic Chemistry, 1990, vol. 55, # 19, p. 5344 - 5347
[2] European Journal of Organic Chemistry, 2009, # 26, p. 4458 - 4467
[3] Patent: WO2008/115516, 2008, A2, . Location in patent: Page/Page column 65
[4] Patent: WO2005/123724, 2005, A1, . Location in patent: Page/Page column 73
[5] Heterocycles, 1999, vol. 51, # 8, p. 1883 - 1889
[6] Organic Letters, 2007, vol. 9, # 26, p. 5429 - 5432
[7] Patent: US2012/214837, 2012, A1, . Location in patent: Page/Page column 40
[8] Journal of the Chemical Society, 1951, p. 1145,1147
[9] Tetrahedron, 2000, vol. 56, # 15, p. 2239 - 2246
[10] Journal of Medicinal Chemistry, 2006, vol. 49, # 25, p. 7493 - 7501
[11] Patent: US5866549, 1999, A,
[12] Patent: US5089495, 1992, A,
[13] Patent: US4888427, 1989, A,
[14] Patent: EP381375, 1990, A1,
[15] Journal of Medicinal Chemistry, 2007, vol. 50, # 24, p. 6116 - 6125
[16] Journal of Medicinal Chemistry, 2008, vol. 51, # 3, p. 449 - 469
[17] Patent: WO2009/66084, 2009, A1, . Location in patent: Page/Page column 98
[18] Patent: WO2004/67502, 2004, A1, . Location in patent: Page 14
[19] Patent: WO2010/132999, 2010, A1, . Location in patent: Page/Page column 92
[20] Journal of Medicinal Chemistry, 2014, vol. 57, # 21, p. 9042 - 9064
[21] Patent: WO2016/86200, 2016, A1, . Location in patent: Page/Page column 223; 224
[22] Patent: JP2015/38095, 2015, A, . Location in patent: Paragraph 0297; 0298
[23] EJNMMI Research, 2018, vol. 8,
[24] Patent: WO2008/38018, 2008, A1, . Location in patent: Page/Page column 58-59
  • 18
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  • [ 13669-51-7 ]
  • [ 79180-47-5 ]
Reference: [1] Collection of Czechoslovak Chemical Communications, 1981, vol. 46, # 6, p. 1518 - 1522
  • 19
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Reference: [1] Synthetic Communications, 2001, vol. 31, # 14, p. 2195 - 2198
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