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Chemical Structure| 254-79-5
Chemical Structure| 254-79-5
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Product Details of [ 254-79-5 ]

CAS No. :254-79-5 MDL No. :MFCD00039727
Formula : C8H6N2 Boiling Point : -
Linear Structure Formula :- InChI Key :VMLKTERJLVWEJJ-UHFFFAOYSA-N
M.W : 130.15 Pubchem ID :136070
Synonyms :

Calculated chemistry of [ 254-79-5 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 39.54
TPSA : 25.78 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) : -6.23 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.48
Log Po/w (XLOGP3) : 1.22
Log Po/w (WLOGP) : 1.63
Log Po/w (MLOGP) : 0.87
Log Po/w (SILICOS-IT) : 2.05
Consensus Log Po/w : 1.45

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.16
Solubility : 0.91 mg/ml ; 0.00699 mol/l
Class : Soluble
Log S (Ali) : -1.36
Solubility : 5.7 mg/ml ; 0.0438 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -3.29
Solubility : 0.0667 mg/ml ; 0.000513 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.27

Safety of [ 254-79-5 ]

Signal Word:Danger Class:9
Precautionary Statements:P264-P270-P273-P280-P301+P312+P330-P305+P351+P338+P310-P501 UN#:3077
Hazard Statements:H302-H318-H412 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 254-79-5 ]

* 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.

  • Upstream synthesis route of [ 254-79-5 ]
  • Downstream synthetic route of [ 254-79-5 ]

[ 254-79-5 ] Synthesis Path-Upstream   1~18

  • 1
  • [ 462-08-8 ]
  • [ 56-81-5 ]
  • [ 254-79-5 ]
YieldReaction ConditionsOperation in experiment
45% With sulfuric acid; sodium 3-nitrobenzenesulfonate In water at 150℃; for 2.5 h; 1,5-Naphthyridine (4) A flask was charged withcompound 3 (1 g, 10.63 mmol), m-NO2PhSO3Na (3.59 g, 15.95 mmol),glycerol (3.33 mL, 46.85 mmol), H2SO4 (5.92 mL, 111.53mmol) and 3 mL water. The mixture was heated to 150°C and stirred for 2.5 h,then cooled to room temperature, basified with NaOH (4 M) to pH 8, and extractedwith EA (5×30 mL). The combined extracts were washed with brine, driedover anhydrous Na2SO4, and concentrated in vacuum.Purification by chromatography (PE/EA = 1:1) provided compound 4 (622 mg, 45percent) as a yellow solid. MP:74~75°C (Ref.1 75°C).1H NMR (400 MHz, CDCl3): δ 9.04–8.96 (m, 2H), 8.43 (d, J = 8.4 Hz, 2H), 7.66 (dd, J= 8.4, 4.1 Hz, 2H).
Reference: [1] Synthetic Communications, 2011, vol. 41, # 12, p. 1843 - 1851
[2] Tetrahedron Letters, 2002, vol. 43, # 20, p. 3747 - 3750
[3] Organic Letters, 2000, vol. 2, # 7, p. 875 - 878
[4] Chemistry - A European Journal, 2017, vol. 23, # 53, p. 13046 - 13050
[5] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 16, p. 3251 - 3255
[6] Crystal Growth and Design, 2017, vol. 17, # 12, p. 6793 - 6800
[7] Chemische Berichte, 1927, vol. 60, p. 1083[8] Chem. Zentralbl., 1928, vol. 99, # I, p. 2093
[9] Journal of the Chemical Society, 1954, p. 1879,1882
[10] Journal of Organic Chemistry, 1950, vol. 15, p. 1224,1231
  • 2
  • [ 462-08-8 ]
  • [ 254-79-5 ]
Reference: [1] Patent: US4092418, 1978, A,
[2] Patent: US4092320, 1978, A,
[3] Patent: US3960876, 1976, A,
  • 3
  • [ 198549-21-2 ]
  • [ 254-79-5 ]
  • [ 13993-61-8 ]
Reference: [1] Tetrahedron Letters, 1997, vol. 38, # 43, p. 7499 - 7502
[2] Journal of Organic Chemistry, 2004, vol. 69, # 21, p. 7171 - 7182
  • 4
  • [ 198549-12-1 ]
  • [ 254-79-5 ]
Reference: [1] Journal of Organic Chemistry, 2004, vol. 69, # 21, p. 7171 - 7182
[2] Tetrahedron Letters, 1997, vol. 38, # 43, p. 7499 - 7502
  • 5
  • [ 791856-59-2 ]
  • [ 254-79-5 ]
Reference: [1] Journal of Organic Chemistry, 2004, vol. 69, # 21, p. 7171 - 7182
  • 6
  • [ 254-79-5 ]
  • [ 17965-80-9 ]
Reference: [1] Journal of the Chemical Society, 1954, p. 1879,1882
[2] Journal of Organic Chemistry, 1981, vol. 46, # 10, p. 2134 - 2137
  • 7
  • [ 254-79-5 ]
  • [ 7689-62-5 ]
Reference: [1] Journal of the Chemical Society, 1954, p. 1879,1882
[2] Patent: WO2009/155121, 2009, A2,
  • 8
  • [ 254-79-5 ]
  • [ 7689-62-5 ]
  • [ 7689-63-6 ]
Reference: [1] Journal of Medicinal Chemistry, 2011, vol. 54, # 13, p. 4735 - 4751
  • 9
  • [ 254-79-5 ]
  • [ 10261-82-2 ]
Reference: [1] Journal of the Chemical Society, 1954, p. 1879,1882
[2] Journal of the Chemical Society, 1954, p. 1879,1882
  • 10
  • [ 254-79-5 ]
  • [ 13993-61-8 ]
Reference: [1] Angewandte Chemie - International Edition, 2017, vol. 56, # 12, p. 3216 - 3220[2] Angew. Chem., 2017, vol. 129, # 12, p. 3264 - 3268,5
[3] Catalysis Science and Technology, 2017, vol. 7, # 10, p. 1981 - 1985
[4] Organic Letters, 2016, vol. 18, # 17, p. 4250 - 4253
[5] Journal of the American Chemical Society, 2015, vol. 137, # 36, p. 11718 - 11724
[6] Tetrahedron Letters, 2001, vol. 42, # 37, p. 6451 - 6454
[7] Yakugaku Zasshi, 1942, vol. 62, p. 257,265; dtsch. Ref. S. 66[8] Chem.Abstr., 1951, p. 2950
[9] Patent: WO2006/76644, 2006, A2, . Location in patent: Page/Page column 175-176
[10] Patent: US4092418, 1978, A,
[11] RSC Advances, 2013, vol. 3, # 46, p. 23984 - 23988
[12] ACS Catalysis, 2015, vol. 5, # 11, p. 6350 - 6354
[13] Organometallics, 2016, vol. 35, # 7, p. 943 - 949
[14] Patent: US3960876, 1976, A,
  • 11
  • [ 254-79-5 ]
  • [ 13993-61-8 ]
Reference: [1] Patent: US4092320, 1978, A,
  • 12
  • [ 198549-21-2 ]
  • [ 254-79-5 ]
  • [ 13993-61-8 ]
Reference: [1] Tetrahedron Letters, 1997, vol. 38, # 43, p. 7499 - 7502
[2] Journal of Organic Chemistry, 2004, vol. 69, # 21, p. 7171 - 7182
  • 13
  • [ 254-79-5 ]
  • [ 17965-71-8 ]
YieldReaction ConditionsOperation in experiment
55% With bromine; sodium acetate In acetic acid at 85℃; for 5 h; 3-Bromo-1,5-naphthyridine (5) To a stirring solutionof compound 4 (2.7 g, 20.76 mmol) and NaOAc(3.41 g,41.52 mmol) in 10 mL glacial AcOH at 85°C was added a solution of Br2 (1 M) in AcOH (35 mL) for 5 h,then cooled to room temperature and concentrated in vacuum to remove AcOH.Purification by chromatography (PE/EA = 2:1) provided compound 5 (2.36 g, 55percent) as a whitesolid. MP: 107~108°C (Ref.2 108~109°C).1H NMR (400 MHz,CDCl3): δ 8.96 (d, J = 2.1 Hz, 2H), 8.56 (s, 1H), 8.36 (d, J = 8.5 Hz, 1H), 7.69–7.56 (m, 1H).
45% With bromine; sodium acetate In acetic acid at 80 - 90℃; for 2 h; To a stirred mixture of 1,5-naphthyridine (C-1) (50.0 g, 384 mmol, 1.0 eq) and sodium acetate(62.9 g, 768 mmol, 2.0 eq) in acetic acid (300 mL) at 80 °C, a solution of bromine (67.5 g, 422 mmol, 1.1 eq) in acetic acid (80 mL) was added dropwise while keeping the reaction temperature at 80 °C to 90 °C. After stirring for 2 h at 80 °C, the reaction was complete based on TLC analysis. The resulting mixture was cooled to RT and then filtered. The filtrate was concentrated in vacuo and the residue was purified by flash column chromatography on silica gel (0-30percent ethyl acetate-petroether) to afford the desired product 3-bromo-l,5-naphthyridine (C-2) (36.5 g, 45 percent yield ) as a pale yellow solid. :H NMR (300 MHz, CDCl3-<3/4) δ: 8.97 (m, 2H), 8.57 (s, 1H), 8.37 (d, J = 8.4 Hz, 1H), 7.65 (m, 1H); ESI-MS m/z : 208.96 [M+H]+.
45% at 80 - 90℃; for 2 h; Example la: Synthesis of 3-bromo-l,5-naphthyridine (C-2) [00305] To a stirred mixture of 1,5-naphthyridine (C-1) (50.0 g, 384 mmol, 1.0 eq) and sodium acetate(62.9 g, 768 mmol, 2.0 eq) in acetic acid (300 mL) at 80 °C, a solution of bromine (67.5 g, 422 mmol, 1.1 eq) in acetic acid (80 mL) was added dropwise while keeping the reaction temperature at 80 °C to 90 °C. After stirring for 2 h at 80 °C, the reaction was complete based on TLC analysis. The resulting mixture was cooled to RT and then filtered. The filtrate was concentrated in vacuo and the residue was purified by flash column chromatography on silica gel (0-30percent ethyl acetate-petroether) to afford the desired product 3-bromo-l,5-naphthyridine (C-2) (36.5 g, 45 percent yield ) as a pale yellow solid. lR NMR (300 MHz, CDC13- (5) δ: 8.97 (m, 2H), 8.57 (s, 1H), 8.37 (d, J = 8.4 Hz, 1H), 7.65 (m, 1H); ESI-MS m/z : 208.96 [M+H]+.
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 16, p. 3251 - 3255
[2] Patent: WO2011/149937, 2011, A1, . Location in patent: Page/Page column 39; 75
[3] Patent: WO2013/78441, 2013, A1, . Location in patent: Paragraph 00143; 00305
[4] Patent: WO2008/82487, 2008, A2, . Location in patent: Page/Page column 108
[5] Patent: WO2011/15343, 2011, A1, . Location in patent: Page/Page column 40
[6] Patent: WO2014/151147, 2014, A1, . Location in patent: Paragraph 00641
[7] Patent: US2015/30588, 2015, A1, . Location in patent: Page/Page column 63
[8] Patent: WO2015/65937, 2015, A1, . Location in patent: Paragraph 000712
[9] Patent: US9295673, 2016, B2, . Location in patent: Page/Page column 335; 336
  • 14
  • [ 254-79-5 ]
  • [ 17965-72-9 ]
  • [ 17965-71-8 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 23, p. 6525 - 6528
  • 15
  • [ 254-79-5 ]
  • [ 17965-72-9 ]
YieldReaction ConditionsOperation in experiment
44% With bromine; sodium acetate In acetic acid at 60℃; for 22.5 h; Intermediate 3. 3,7-Dibromo-1,5-naphthyridine
1,5-Naphthyridine (30.80 g, 236.7 mmol) and sodium acetate (38.83 g, 473.3 mmol) were dissolved in acetic acid (236.7 mL) and heated to 60° C. A solution of bromine (25.6 mL, 496.9 mmol) in acetic acid (35 mL) was added dropwise over 30 minutes.
The solution was allowed to stir for 22 h at 60° C.
The reaction was cooled to ambient temperature then diluted with water (250 mL) and basified with 4 N NaOH (aq.) (300 mL), where upon addition of base, a beige precipitate formed.
The precipitate was collected by filtration then washed with water, MeOH, and acetone.
The remaining solid (54.7 g) was recrystallized from chloroform (1.36 L) to give the title compound as a pure, cream colored solid (30 g, 44percent).
1H NMR (400 MHz, CDCl3) δ 9.08-8.95 (m, 2H), 8.62 (dd, J=2.2, 0.7 Hz, 1H), 8.46-8.35 (m, 1H), 8.23 (d, J=8.8 Hz, 1H), 7.79 (d, J=8.8 Hz, 1H), 7.69 (dd, J=8.5, 4.3 Hz, 1H).
[M+H]=286.9.
Reference: [1] Patent: US2014/275548, 2014, A1, . Location in patent: Paragraph 0370; 0371
  • 16
  • [ 254-79-5 ]
  • [ 17965-72-9 ]
  • [ 17965-71-8 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 23, p. 6525 - 6528
  • 17
  • [ 254-79-5 ]
  • [ 959616-36-5 ]
Reference: [1] Patent: WO2011/149937, 2011, A1,
[2] Patent: WO2013/78441, 2013, A1,
[3] Patent: WO2014/151147, 2014, A1,
[4] Patent: US2015/30588, 2015, A1,
[5] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 16, p. 3251 - 3255
[6] Patent: US9295673, 2016, B2,
  • 18
  • [ 254-79-5 ]
  • [ 1309774-03-5 ]
Reference: [1] Patent: WO2011/149937, 2011, A1,
[2] Patent: WO2013/78441, 2013, A1,
[3] Patent: WO2014/151147, 2014, A1,
[4] Patent: US2015/30588, 2015, A1,
[5] Patent: US9295673, 2016, B2,
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