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[ CAS No. 1057682-05-9 ] {[proInfo.proName]}

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Chemical Structure| 1057682-05-9
Chemical Structure| 1057682-05-9
Structure of 1057682-05-9 * Storage: {[proInfo.prStorage]}
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Product Details of [ 1057682-05-9 ]

CAS No. :1057682-05-9 MDL No. :MFCD17488802
Formula : C11H14N4 Boiling Point : -
Linear Structure Formula :- InChI Key :USAKGOYBWIQOPV-SECBINFHSA-N
M.W : 202.26 Pubchem ID :44186481
Synonyms :

Calculated chemistry of [ 1057682-05-9 ]

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.45
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 65.12
TPSA : 51.95 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) : -6.97 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.95
Log Po/w (XLOGP3) : 0.8
Log Po/w (WLOGP) : -0.01
Log Po/w (MLOGP) : 0.32
Log Po/w (SILICOS-IT) : 1.12
Consensus Log Po/w : 0.83

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.83
Solubility : 3.01 mg/ml ; 0.0149 mol/l
Class : Very soluble
Log S (Ali) : -1.47
Solubility : 6.82 mg/ml ; 0.0337 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.77
Solubility : 0.343 mg/ml ; 0.0017 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.66

Safety of [ 1057682-05-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338-P310 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1057682-05-9 ]

* 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 [ 1057682-05-9 ]
  • Downstream synthetic route of [ 1057682-05-9 ]

[ 1057682-05-9 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 33252-28-7 ]
  • [ 75336-86-6 ]
  • [ 1057682-05-9 ]
YieldReaction ConditionsOperation in experiment
69% With potassium carbonate In acetonitrile at 20 - 60℃; for 2 h; To a mixture of 6-chloropyridine-3-carbonitrile (10 g, 0.06 mol) and (2R)-2-methylpiperazine(6.35 g, 0.06 mol) in acetonitrile (80 mL), K2C03 (12.0 g, 0.09 mol) was added at RT. Theresulting mixture was stirred at 60°C for 2 h (TLC indicated complete consumption ofstarting material). The reaction was brought toRT, quenched with water (150 mL) andextracted with EtOAc (3 x 80 mL). The combined organic extracts were dried over anhydrousNa2S04 and concentrated under reduced pressure. The residue was purified by columnchromatography (100-200 silica gel, 5percent MeOH-DCM) to afford 6-[(3R)-3-methylpiperazine-1-yl]-pyridine-3-carbonitrile (10.0 g, 69percent yield).
59% With triethylamine In N,N-dimethyl-formamide at 20℃; for 36 h; Triethylamine (5.51 g, 4 mL, 54.6 mmol, 2.7 eq) is added to a solution of 6-chloro- nicotinonitrile (2.76 g, 20 mmol, 1 eq), (i?)-2-methyl- piperazine (2.0Og, 20 mmol, 1 eq) in DMF (15 mL), and the resulting solution is stirred at rt for 36 h. A white precipitate of triethylamine hydrochloride forms in the course of the reaction. Water (15 mL) and EtOAc (100 mL) are added, the organic layer is separated, dried over sodium sulfate and concentrated under reduced pressure to a white residue. The solid is further dried under high vacuum to yield the desired product as a white solid (2.3 g, 59percent). IH NMR (400 MHz, CHLOROFORM-*/) δ ppm 8.32 (d, J=2.40 Hz, 1 H), 7.52 (dd, J=9.09, 2.27 Hz, 1 H), 6.52 (d, J=8.97 Hz, 1 H), 4.14 - 4.24 (m, 2 H), 3.01 - 3.07 (m, 1 H), 2.72 - 2.94 (m, 3 H), 2.52 (dd, J=12.76, 10.36 Hz, 1 H), 1.07 (d, J=6.32 Hz, 3 H).
Reference: [1] Patent: WO2018/125961, 2018, A1, . Location in patent: Page/Page column 80
[2] Journal of Medicinal Chemistry, 2009, vol. 52, # 13, p. 3954 - 3968
[3] Patent: WO2008/110611, 2008, A1, . Location in patent: Page/Page column 34
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