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[ CAS No. 142253-54-1 ] {[proInfo.proName]}

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Chemical Structure| 142253-54-1
Chemical Structure| 142253-54-1
Structure of 142253-54-1 * Storage: {[proInfo.prStorage]}
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Product Details of [ 142253-54-1 ]

CAS No. :142253-54-1 MDL No. :MFCD06796640
Formula : C9H14N2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :WEFREESWPHICPL-UHFFFAOYSA-N
M.W : 182.22 Pubchem ID :10631283
Synonyms :

Calculated chemistry of [ 142253-54-1 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.78
Num. rotatable bonds : 3
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 51.53
TPSA : 53.33 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) : -6.98 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.1
Log Po/w (XLOGP3) : 0.61
Log Po/w (WLOGP) : 1.0
Log Po/w (MLOGP) : 0.45
Log Po/w (SILICOS-IT) : 0.48
Consensus Log Po/w : 0.93

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.16
Solubility : 12.7 mg/ml ; 0.0698 mol/l
Class : Very soluble
Log S (Ali) : -1.3
Solubility : 9.05 mg/ml ; 0.0496 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.8
Solubility : 28.8 mg/ml ; 0.158 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.22

Safety of [ 142253-54-1 ]

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

Application In Synthesis of [ 142253-54-1 ]

* 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 [ 142253-54-1 ]
  • Downstream synthetic route of [ 142253-54-1 ]

[ 142253-54-1 ] Synthesis Path-Upstream   1~11

  • 1
  • [ 345954-83-8 ]
  • [ 24424-99-5 ]
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YieldReaction ConditionsOperation in experiment
98% With triethylamine In dichloromethane for 16 h; Step 1
3-Cyanoazetidine hydrochloride (3.64 g, 30.7 mmol) was suspended in 77 mL of dichloromethane.
Triethylamine (4.3 mL, 30.7 mmol) was added, followed by portionwise addition of di-tert-butyl dicarbonate (8.0 g, 36.8 mmol).
The reaction mixture was stirred for 16 h then diluted with aqueous hydrochloric acid and dichloromethane.
The layers were separated and the aqueous layer was extracted with dichloromethane.
The combined organic layers were washed with sodium chloride solution, dried over magnesium sulfate, and evaporated.
The residue was purified by silica gel chromatography (ethyl acetate/hexanes) to give 5.5 g (98percent) of tert-butyl 3-cyanoazetidine-1-carboxylate.
Reference: [1] Patent: US2011/230462, 2011, A1, . Location in patent: Page/Page column 64-65
[2] Patent: WO2011/61214, 2011, A1, . Location in patent: Page/Page column 50
[3] Patent: WO2013/152065, 2013, A2, . Location in patent: Page/Page column 27
  • 2
  • [ 773837-37-9 ]
  • [ 254454-54-1 ]
  • [ 142253-54-1 ]
YieldReaction ConditionsOperation in experiment
78% at 130℃; for 6 h; To a 100 mL round bottom flask was added tert-butyl 3-iodoazetidine-1-carboxylate (6) (6.54 g, 0.0231 mol, 1 equiv.) and DMSO (25 mL). NaCN (2.3 g, 0.0462 mol, 2equiv.) was added to the solution in one portion and stirred at 130 oC for 6 h. The resulting mixture was cooledto rt, poured into water (200 mL), and extracted with diethyl ether (5 x 200 mL). The combined organicextracts were washed with brine (50 mL), dried over Na2SO4 and concentrated. The crude compound waspurified by flash chromatography (silica gel, 5–50percent EtOAc in hexanes) to give the desired product 22 (3.27 g,78percent). Physical State: off-white solid (mp 78–80 oC); Rf = 0.40 (2:8 EtOAc/hexanes, vis. KMnO4); 1H NMR (500MHz, CDCl3): δ 4.23 – 4.11 (m, 4H), 3.38 (tt, J 8.9, 6.3 Hz, 1H), 1.43 (s, 9H); 13C NMR (126 MHz, CDCl3): δ 155.6,119.6, 80.8, 52.6 (br, 2C), 28.4 (3C), 17.2.
Reference: [1] Arkivoc, 2018, vol. 2018, # 4, p. 195 - 214
  • 3
  • [ 773837-37-9 ]
  • [ 124-63-0 ]
  • [ 141699-55-0 ]
  • [ 142253-54-1 ]
Reference: [1] Patent: US2003/229226, 2003, A1, . Location in patent: Page 20
  • 4
  • [ 773837-37-9 ]
  • [ 141699-58-3 ]
  • [ 142253-54-1 ]
Reference: [1] Patent: WO2010/131145, 2010, A1, . Location in patent: Page/Page column 85-86
[2] Patent: WO2016/206101, 2016, A1, . Location in patent: Page/Page column 89
  • 5
  • [ 143-33-9 ]
  • [ 141699-58-3 ]
  • [ 142253-54-1 ]
Reference: [1] Journal of Medicinal Chemistry, 2001, vol. 44, # 1, p. 94 - 104
  • 6
  • [ 141699-55-0 ]
  • [ 142253-54-1 ]
Reference: [1] Journal of Medicinal Chemistry, 2001, vol. 44, # 1, p. 94 - 104
[2] Patent: WO2016/206101, 2016, A1,
  • 7
  • [ 142253-54-1 ]
  • [ 325775-44-8 ]
Reference: [1] Journal of Medicinal Chemistry, 2001, vol. 44, # 1, p. 94 - 104
[2] Patent: US2003/229226, 2003, A1, . Location in patent: Page 20
  • 8
  • [ 142253-54-1 ]
  • [ 142253-55-2 ]
YieldReaction ConditionsOperation in experiment
92% With sodium hydroxide In methanol; water for 4 h; Reflux To a solution of tert-butyl 3-cyanoazetidine-1-carboxylate 22 (3.7 g, 0.0202 mol, 1 equiv.) in MeOH (35 mL) was added a solution of NaOH (4.03 g, 0.101 mol,5 equiv.) in H2O (35 mL) and refluxed until the reaction was complete by TLC (ca. 4 h). The resulting reactionmixture was cooled to rt and concentrated to remove the MeOH. The mixture was neutralized with 10 percent aq.citric acid (200 mL) and extracted with CH2Cl2 (3 x 50 mL). The combined organic layers were washed withbrine (50 mL), dried over Na2SO4, and concentrated to give the desired product 23 (3.72 g, 92percent). PhysicalState: white solid (mp 106–107 oC); 1H NMR (500 MHz, CDCl3): δ 4.13 (d, J 7.5 Hz, 4H), 3.41 – 3.35 (m, 1H), 1.44(s, 9H); 13C NMR (126 MHz, CDCl3): δ 177.4, 155.3, 80.3, 51.8 (br, 2C), 32.0, 28.5 (3C); HRMS (ESI-TOF): calc’dfor C9H14NO4 [M-H] 200.0928; found 200.0923.
80.8%
Stage #1: With water; sodium hydroxide In methanol for 5 h; Reflux
Stage #2: With citric acid In water
Preparation 831 -(tert-ButoxycarbonvDazetidine-S-carboxylic acid; A solution of sodium hydroxide (27.5 g) in water (30OmL) was added to solution of tert-butyl 3- cyanoazetidine-1-carboxylate (Preparation 82, 25.1 g, 0.138 mol) in methanol (30OmL). The mixture was heated at reflux for 5 hours. The methanol was evaporated and the residuary aqueous solution was neutralized with 10percent citric acid and extracted with dichloromethane (2.1 L). The combined organic extracts were dried over magnesium sulfate and concentrated in vacuo to afford the title compound as a white crystalline solid (22.3 g, 80.8percent). 1H NMR (400 MHz, DMSO-d6): δ = 4.01-3.97 (m, 2H), 3.87-3.84 (m, 2H), 3.36-3.28 (m, 1 H), 1.37 (s, 9H) ppm.
Reference: [1] Arkivoc, 2018, vol. 2018, # 4, p. 195 - 214
[2] Patent: WO2010/131145, 2010, A1, . Location in patent: Page/Page column 86
  • 9
  • [ 142253-54-1 ]
  • [ 345954-83-8 ]
Reference: [1] Patent: WO2010/60952, 2010, A1, . Location in patent: Page/Page column 107-108
  • 10
  • [ 142253-54-1 ]
  • [ 345954-83-8 ]
Reference: [1] Patent: CN105732602, 2016, A, . Location in patent: Paragraph 0458; 0459; 0460; 0461; 0462; 0463
  • 11
  • [ 142253-54-1 ]
  • [ 887591-62-0 ]
Reference: [1] Arkivoc, 2018, vol. 2018, # 4, p. 195 - 214
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