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[ CAS No. 1314910-43-4 ] {[proInfo.proName]}

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Chemical Structure| 1314910-43-4
Chemical Structure| 1314910-43-4
Structure of 1314910-43-4 * Storage: {[proInfo.prStorage]}
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Product Details of [ 1314910-43-4 ]

CAS No. :1314910-43-4 MDL No. :MFCD19227479
Formula : C5H7ClN2 Boiling Point : -
Linear Structure Formula :- InChI Key :XELKWDFNWRGTLX-UHFFFAOYSA-N
M.W : 130.58 Pubchem ID :55300440
Synonyms :

Calculated chemistry of [ 1314910-43-4 ]

Physicochemical Properties

Num. heavy atoms : 8
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.4
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 36.99
TPSA : 35.82 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.23 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : -0.19
Log Po/w (WLOGP) : 0.46
Log Po/w (MLOGP) : -0.04
Log Po/w (SILICOS-IT) : 0.9
Consensus Log Po/w : 0.23

Druglikeness

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

Water Solubility

Log S (ESOL) : -0.53
Solubility : 38.5 mg/ml ; 0.295 mol/l
Class : Very soluble
Log S (Ali) : -0.11
Solubility : 102.0 mg/ml ; 0.783 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.79
Solubility : 21.3 mg/ml ; 0.163 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.26

Safety of [ 1314910-43-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1314910-43-4 ]

* 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 [ 1314910-43-4 ]
  • Downstream synthetic route of [ 1314910-43-4 ]

[ 1314910-43-4 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 1314910-43-4 ]
  • [ 594-44-5 ]
  • [ 1187595-85-2 ]
YieldReaction ConditionsOperation in experiment
98.59%
Stage #1: With N-ethyl-N,N-diisopropylamine In acetonitrile at 0 - 10℃; for 0.166667 h;
Stage #2: at 0 - 25℃; for 16 h;
N,N-Diisopropylethylamine (4.5 mL) was added into a reaction vessel containing acetonitrile (50 mL) and 3-(cyanomethylene)azetidine hydrochloride (1.5 g; Formula VII) at about 0°C to about 10°C. The reaction mixture was stirred for about 10 minutes. Ethanesulfonyl chloride (2.22 g) was added into the reaction mixture at about 0°C to about 5°C over about 5 minutes. The temperature of the reaction mixture was raised to about 20°C to about 25 °C, and then the reaction mixture was stirred for about 16 hours. On completion of the reaction, acetonitrile was recovered from the reaction mixture under reduced pressure at about 40°C to about 45°C to obtain an oily residue. Dichloromethane (50 mL) was added into the residue. The contents were washed with a saturated sodium chloride solution (30 mL), followed by complete recovery of dichloromethane under reduced pressure at about 40°C to obtain 2-(l-(ethylsulfonyl)azetidin-3- ylidene)acetonitrile . Yield: 98.59percent
Reference: [1] Patent: WO2016/125080, 2016, A2, . Location in patent: Page/Page column 11
[2] Patent: US2009/233903, 2009, A1, . Location in patent: Page/Page column 63-64
[3] Patent: WO2013/40863, 2013, A1, . Location in patent: Page/Page column 109-110
[4] Patent: US2016/333015, 2016, A1, . Location in patent: Paragraph 0055; 0057; 0134; 0136
  • 2
  • [ 1314910-43-4 ]
  • [ 1379208-59-9 ]
  • [ 594-44-5 ]
  • [ 1187595-85-2 ]
  • [ 1187595-86-3 ]
Reference: [1] Patent: US2009/233903, 2009, A1, . Location in patent: Page/Page column 58-60
  • 3
  • [ 1153949-11-1 ]
  • [ 1314910-43-4 ]
YieldReaction ConditionsOperation in experiment
90% With hydrogenchloride In 1,4-dioxane for 2.5 h; Inert atmosphere; Cooling with ice General procedure: Compound 1d (1.0 g, 5.15 mmol) and a 4M solution of HCI in dioxane (10 mL) were added to a 50 mL reaction flask, argon atmosphere protection was applied, and the reaction was stirred in an ice bath for 2.5 h, while white solid gradually precipitated.
The reaction was monitored by thin layer chromatography.
After the reaction was complete, the reaction solution was filtered with suction, and the filter cake was washed with anhydrous ether and dried, to afford 2-(azetidin-3-ylidene) acetonitrile hydrochloride salt (1e) (600 mg, yield: 90.0percent, white solid), which was used directly in the next reaction.
75% With hydrogenchloride In methanol; waterReflux Aqueous hydrochloric acid (6N, 10 mL) and montmorillonite K-10 (2 g) were added into a reaction vessel at ambient temperature. The contents were stirred for 1 hour, and then filtered under reduced pressure to obtain activated montmorillonite K-10. The activated montmorillonite K-10 was added into another reaction vessel containing tert- butyl 3-(cyanomethylidene)azetidine-l-carboxylate (2 g; Formula VI) and methanol (20 mL) at ambient temperature. The reaction mixture was refluxed for about 12 hours to about 15 hours. On completion, the reaction mixture was filtered under reduced pressure followed by recovery of methanol under reduced pressure at about 40°C to about 45°C to obtain 3-(cyanomethylene)azetidine hydrochloride. Yield: 75percent
67.8% With hydrogenchloride In isopropyl alcohol at 20℃; for 18 h; Inert atmosphere 2-(Azetidin-3-ylidene)acetonitrile hydrochloride (2a) [0145] To a 0.5-L flask equipped with a nitrogen inlet, a thermocouple, and a mechanical stirrer were added tert-butyl 3-(cyanomethylene)azetidine-1-carboxylate (2, 30 g, 154.46 mmol) and methylenechloride (300 mL) at ambient temperature. The solution was then treated with a solution of 5 M hydrogen chloride (HCl) in isopropanol solution (294.2 mL, 1.54 mol, 10 equiv) at ambient temperature and the resulting reaction mixture was stirred at ambient temperature for 18 hours. After the reaction was complete as monitored by HPLC, the suspension was added tert-butyl methyl ether (TBME, 150 mL), and the mixture was stirred at ambient temperature for 2 hours. The solids was collected by filtration, washed with n-heptane (2×100 mL), and dried on the filtration funnel at ambient temperature for 3 hours to afford 2-(azetidin-3-ylidene)acetonitrile hydrochloride (2a, 13.7 g, 20.2 g theoretical, 67.8percent) as a white solid. For 2a: 1H NMR (500 MHz, DMSO-d6) δ 9.99 (s, 2H), 5.94 (p, J=2.5 Hz, 1H), 4.85-4.80 (m, 2H), 4.77-4.71 (m, 2H) ppm; 13C NMR (126 MHz, DMSO-d6) δ 155.65, 114.54, 94.78, 55.26, 54.63 ppm; C5H7ClN2 (MW 130.58; C5H6N2 for free base, MW 94.11), LCMS (EI) m/e 95 (M++H).
Reference: [1] Patent: EP3360878, 2018, A1, . Location in patent: Paragraph 0082; 0085; 0151; 0154; 0158; 0161; 0165; 0168
[2] Patent: WO2016/125080, 2016, A2, . Location in patent: Page/Page column 10; 11
[3] Patent: US2014/256941, 2014, A1, . Location in patent: Paragraph 0145
[4] Patent: US2009/233903, 2009, A1, . Location in patent: Page/Page column 63-64
[5] Patent: WO2013/40863, 2013, A1, . Location in patent: Page/Page column 109-110
[6] Patent: US2016/333015, 2016, A1, . Location in patent: Paragraph 0055; 0057; 0081; 0083; 0105; 0107; 0134; 0136
  • 4
  • [ 1153949-11-1 ]
  • [ 1314910-43-4 ]
  • [ 1379208-59-9 ]
Reference: [1] Patent: US2009/233903, 2009, A1, . Location in patent: Page/Page column 58-60
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