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[ CAS No. 131052-40-9 ] {[proInfo.proName]}

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Chemical Structure| 131052-40-9
Chemical Structure| 131052-40-9
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Product Details of [ 131052-40-9 ]

CAS No. :131052-40-9 MDL No. :MFCD16036517
Formula : C12H16N2O4 Boiling Point : -
Linear Structure Formula :- InChI Key :GPVMPPDFEOSPND-UHFFFAOYSA-N
M.W : 252.27 Pubchem ID :14842342
Synonyms :

Calculated chemistry of [ 131052-40-9 ]

Physicochemical Properties

Num. heavy atoms : 18
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.42
Num. rotatable bonds : 6
Num. H-bond acceptors : 5.0
Num. H-bond donors : 1.0
Molar Refractivity : 65.76
TPSA : 77.52 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) : -6.7 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.45
Log Po/w (XLOGP3) : 1.6
Log Po/w (WLOGP) : 2.02
Log Po/w (MLOGP) : 0.76
Log Po/w (SILICOS-IT) : 1.15
Consensus Log Po/w : 1.6

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.26
Solubility : 1.38 mg/ml ; 0.00546 mol/l
Class : Soluble
Log S (Ali) : -2.84
Solubility : 0.365 mg/ml ; 0.00145 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.06
Solubility : 0.221 mg/ml ; 0.000875 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.54

Safety of [ 131052-40-9 ]

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

Application In Synthesis of [ 131052-40-9 ]

* 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 [ 131052-40-9 ]
  • Downstream synthetic route of [ 131052-40-9 ]

[ 131052-40-9 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 131052-40-9 ]
  • [ 323578-38-7 ]
YieldReaction ConditionsOperation in experiment
67% With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 12 h; Inert atmosphere Step 3. tert-Butyl (6-(hydroxymethyl)pyridin-3-yl)carbamate. LAH powder (36 g, 0.96 mol) was suspended in dry THF (1000 ml) under N2 atmosphere and cooled to 0° C. To the mixture was added compound 3 (150 g, 0.60 mol) in dry THF (1000 ml) slowly at 0° C. The reaction mixture was gradually warmed to room temperature and stirred for 12 h. TLC (PE/EA, 1:1) showed that the reaction was complete, and the reaction was quenched with dropwise addition of THF-Water (9:1, 400 mL) followed by 90 ml 15percent NaOH aqueous and 50 ml of water at 0° C., stirred for 0.5 h at room temperature, and filtered through a pad of Celite®, and then washed with THF (4×1000 ml). The filtrate was concentrated under reduced pressure to give the crude which was purified by column chromatography over silica gel eluting with PE/EA (2:1-1:2). The desired fraction was concentrated to afford tert-butyl (6-(hydroxymethyl)pyridin-3-yl)carbamate (450 g, 67percent) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 9.58-9.40 (m, 1H), 8.59-8.45 (m, 1H), 7.95-7.78 (m, 1H), 7.42-7.22 (m, 1H), 5.42-5.21 (m, 1H), 4.58-4.40 (m, 2H), 1.48 (s, 9H).
60% With lithium aluminium tetrahydride In tetrahydrofuran; diethyl ether at 0 - 20℃; for 12 h; Inert atmosphere To a stirred solution of methyl 5-[(tert-butoxy)carbonyl]amino}pyridine-2- carboxylate (EV-AX4571-001, 2.73 g, 10.82 mmol) in THF (60 ml) at 0 °C under an atmosphere of nitrogen was added 4M lithium tetrahydridoaluminate(l-) in diethyl ether (4.1 ml) drop-wise, the reaction was allowed to warm to room temperature and stirred for a further 12h. The reaction was quenched by addition of THF:water (9: 1, 15 ml), followed by 10percent sodium hydroxide (10 ml) and then water (10 ml). The reaction mixture was then filtered through a pad of Kieselguhr, rinsing with THF (3 x 50 ml). The filtrate was concentrated in vacuo and the crude was purified by flash column chromatography (50-100percent) EtOAc/heptane then 0-10percent Methanol/EtOAc) to obtain 1.50 g (60percent) of tert-butyl N-[6- (hydroxymethyl)pyridin-3-yl]carbamate EV-AX4573-001 as an off-white solid. LCMS (method D): retention time 0.70min, M/z = 224 (M + 1).
Reference: [1] European Journal of Inorganic Chemistry, 2010, # 13, p. 1913 - 1928
[2] Patent: US2015/158864, 2015, A1, . Location in patent: Paragraph 0295
[3] Patent: WO2017/100594, 2017, A1, . Location in patent: Paragraph 00304
[4] Patent: WO2006/51270, 2006, A1, . Location in patent: Page/Page column 146
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