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[ CAS No. 36052-25-2 ] {[proInfo.proName]}

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Chemical Structure| 36052-25-2
Chemical Structure| 36052-25-2
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Product Details of [ 36052-25-2 ]

CAS No. :36052-25-2 MDL No. :MFCD04038688
Formula : C7H8N2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :MBGSRKHDEJNWED-UHFFFAOYSA-N
M.W :152.15 Pubchem ID :1514432
Synonyms :

Calculated chemistry of [ 36052-25-2 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.14
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 39.92
TPSA : 65.21 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.21 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.25
Log Po/w (XLOGP3) : 0.02
Log Po/w (WLOGP) : 0.46
Log Po/w (MLOGP) : -0.26
Log Po/w (SILICOS-IT) : 0.47
Consensus Log Po/w : 0.39

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.07
Solubility : 13.0 mg/ml ; 0.0856 mol/l
Class : Very soluble
Log S (Ali) : -0.94
Solubility : 17.4 mg/ml ; 0.114 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.73
Solubility : 2.87 mg/ml ; 0.0188 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.42

Safety of [ 36052-25-2 ]

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

Application In Synthesis of [ 36052-25-2 ]

* 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 [ 36052-25-2 ]
  • Downstream synthetic route of [ 36052-25-2 ]

[ 36052-25-2 ] Synthesis Path-Upstream   1~11

  • 1
  • [ 36052-25-2 ]
  • [ 27828-71-3 ]
Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1933, vol. <2> 138, p. 244,257
  • 2
  • [ 36052-25-2 ]
  • [ 24242-19-1 ]
Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1933, vol. <2> 138, p. 244,257
  • 3
  • [ 67-56-1 ]
  • [ 24242-19-1 ]
  • [ 36052-25-2 ]
YieldReaction ConditionsOperation in experiment
86% at 0℃; Reflux To a stirred solution of 5-amino-nicotinic acid (10.0 g, 72.5 mmol) in methanol (100 mL) was added SOCl2 (10.4 g, 86.9 mmol) dropwise at 0°C. The mixture was allowed warm to room temperature and then refluxed for 16 hours. The mixture was cooled, concentrated in vacuum and the residue was diluted with water (200 mL). The mixture was neutralized with aqueous NaHC03 solution to pH = 7. The aqueous mixture was extracted with DCM (100 mL x2). The combined organic layers were washed with brine (100 mL x2), dried over anhydrous Na2S04, filtered and the filtrate was concentrated in vacuum to dryness to give 9.5 g (yield: 86percent) of 5-amino-nicotinic acid methyl ester as white solid. 1H NMR (DMSO-d6, 400MHz): δ = 8.24 (1H, d), 8.12 (1H, d), 7.42 (1H, dd), 5.65 (2H, brs), 3.84 (3H, s).
85% at 0 - 20℃; for 18 h; 5-Aminonicotinic acid (1g,.7.2mmmol) was suspended in methanol (100ml) and thionyl chloride (4.22ml, 57.9mmol) added dropwise at O0C. The reaction mixture was stirred at room temperature for 18 h. The reaction mixture was evaporated to dryness and the resultant yellow oil was re-dissolved in methanol/ether (1:1) and afforded yellow crystals (HCI salt) which were collected by filtration, yield 1.2g (85percent). LCMS purity 91percent, m/z 153 [M++H]+,
Reference: [1] Patent: WO2013/126608, 2013, A1, . Location in patent: Paragraph 00492-00493
[2] Patent: WO2006/117549, 2006, A1, . Location in patent: Page/Page column 97
[3] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 22, p. 6305 - 6310
[4] Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 17, p. 6340 - 6350
[5] Chemistry - A European Journal, 2002, vol. 8, # 5, p. 1218 - 1226
[6] Bioorganic and Medicinal Chemistry Letters, 2018, vol. 28, # 1, p. 31 - 34
  • 4
  • [ 24242-19-1 ]
  • [ 36052-25-2 ]
YieldReaction ConditionsOperation in experiment
63% With hydrogenchloride In methanol at 0 - 75℃; for 3 h; Alkaline aqueous solution Over 30 minutes hydrogen chloride gas was bubbled through dry methanol (60 [ML)] cooled to [0-5 C.] Then 5-amino-3-pyridinecarboxylic acid (i. e. the product of Step B) (6.0 g, 43 mmol) was added, and the reaction mixture was heated at [75 C] for 3 h. The reaction mixture was concentrated, the residue was poured into cold water (30 mL), and the pH of the resulting mixture was increased to 4-5 by adding sodium bicarbonate. The mixture was then extracted with ethyl acetate, and the ethyl acetate extract was washed with water and brine, and then dried [(NA2SO4)] and concentrated. The residue was triturated with ethyl acetate-petroleum ether to yield the title compound (4.2 g, 63percent yield).
Reference: [1] Patent: WO2004/35545, 2004, A2, . Location in patent: Page 46
  • 5
  • [ 24242-19-1 ]
  • [ 18107-18-1 ]
  • [ 36052-25-2 ]
Reference: [1] Patent: WO2010/111056, 2010, A1, . Location in patent: Page/Page column 35-36
  • 6
  • [ 20826-04-4 ]
  • [ 36052-25-2 ]
Reference: [1] Chemistry - A European Journal, 2002, vol. 8, # 5, p. 1218 - 1226
  • 7
  • [ 499-81-0 ]
  • [ 36052-25-2 ]
Reference: [1] Patent: WO2009/42694, 2009, A1, . Location in patent: Page/Page column 95
  • 8
  • [ 36052-25-2 ]
  • [ 455-70-9 ]
YieldReaction ConditionsOperation in experiment
56% at 0 - 50℃; for 1.5 h; Example 2.26: methyl 5-fluoronicotinate; [0264] To a stirring solution of 243 mg (1.6 minol) of methyl 5-aminonicotinate in 5 mL of HF-pyridine at 0 0C was added 119 mg (1.72 mmol) OfNaNO2. The mixture was stirred at 0 0C for 30 min. and at 50 0C for 1 h. The reaction was quenched by ice and sat. NaHCO3 solution. The aqueous layer was extracted with CHCl3, dried over Na2SO4, filtered, and concentrated. Purification by flash silica gel chromatography (1percent MeOH/CHCl3) provided 139 mg of methyl 5-fluoronicotinate as a yellow solid in 56percent yield.
Reference: [1] Patent: WO2006/110668, 2006, A1, . Location in patent: Page/Page column 62
[2] Journal of Organic Chemistry, 1949, vol. 14, p. 328,331
[3] Angewandte Chemie - International Edition, 2018, vol. 57, # 31, p. 9896 - 9900[4] Angew. Chem., 2018, vol. 130, p. 10044 - 10048,5
  • 9
  • [ 36052-25-2 ]
  • [ 60524-14-3 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 22, p. 6305 - 6310
  • 10
  • [ 36052-25-2 ]
  • [ 51035-70-2 ]
Reference: [1] Chemistry - A European Journal, 2002, vol. 8, # 5, p. 1218 - 1226
  • 11
  • [ 36052-25-2 ]
  • [ 443649-18-1 ]
YieldReaction ConditionsOperation in experiment
100% With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 21 h; 5-Amino-nicotinic acid methyl ester (5.7g, 30.2mmol) was dissolved in THF (150ml) and LiAIH4 (1 M in THF solution 133ml, 133mmol) added slowly at O0C. The reaction mixture was stirred at room temperature for 21 h. The reaction mixture was quenched and acidified to pH 3 using dilute HCI, and basified (pH 8) using solid Na2CO3. Solvents were removed under reduced pressure. The residue was filtered through silica gel using 20percent MeOH/DCM yielding the product 3.8g, (100percent) with LCMS purity 97percent, m/z 125 [M++H]+, by ELS
Reference: [1] Patent: WO2006/117549, 2006, A1, . Location in patent: Page/Page column 97
[2] Chemistry - A European Journal, 2002, vol. 8, # 5, p. 1218 - 1226
[3] Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 17, p. 6340 - 6350
[4] Patent: WO2018/13774, 2018, A1, . Location in patent: Page/Page column 256; 257
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