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[ CAS No. 343788-69-2 ] {[proInfo.proName]}

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Chemical Structure| 343788-69-2
Chemical Structure| 343788-69-2
Structure of 343788-69-2 * Storage: {[proInfo.prStorage]}
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Product Details of [ 343788-69-2 ]

CAS No. :343788-69-2 MDL No. :MFCD03265497
Formula : C11H22N2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :DMBKWEHXTOCLTC-UHFFFAOYSA-N
M.W : 214.31 Pubchem ID :11310432
Synonyms :

Calculated chemistry of [ 343788-69-2 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.91
Num. rotatable bonds : 3
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 64.15
TPSA : 55.56 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) : -6.96 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.69
Log Po/w (XLOGP3) : 0.91
Log Po/w (WLOGP) : 1.35
Log Po/w (MLOGP) : 1.15
Log Po/w (SILICOS-IT) : 0.8
Consensus Log Po/w : 1.38

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.54
Solubility : 6.12 mg/ml ; 0.0286 mol/l
Class : Very soluble
Log S (Ali) : -1.66
Solubility : 4.66 mg/ml ; 0.0218 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.53
Solubility : 6.35 mg/ml ; 0.0296 mol/l
Class : Soluble

Medicinal Chemistry

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

Safety of [ 343788-69-2 ]

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 [ 343788-69-2 ]

* 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 [ 343788-69-2 ]
  • Downstream synthetic route of [ 343788-69-2 ]

[ 343788-69-2 ] Synthesis Path-Upstream   1~12

  • 1
  • [ 236406-14-7 ]
  • [ 343788-69-2 ]
YieldReaction ConditionsOperation in experiment
90.2% With hydrogen In methanol at 25℃; for 16 h; A mixture of the compound of formula LE (2.48g, 7.1 lmmol) and 10percent palladium on carbon (200mg, Sigma-Aldrich) in methanol (2OmL) was stirred under a hydrogen atmosphere at a temperature of about 250C for 16h. The Pd/C was filtered off and the filtrate was concentrated under reduced pressure to provide 1.37g of the compound of formula LF as a silverery-colored viscous oil (yield 90.2percent). <n="236"/>The identity of the compound of formula LF, tert-butyl 4-amino-4-methylpiperidine-l- carboxylate, was confirmed using 1H NMR.Compound LF: 1H NMR: δH (400 MHz, CDCl3): 3.47-3.49 (4H, m), 1.47-1.61 (4H, m), 1.46 (9H, s), 1.31-1.42 (2H, m), 1.15 (3H, s).
Reference: [1] Patent: WO2008/89201, 2008, A2, . Location in patent: Page/Page column 234-235
[2] Journal of Medicinal Chemistry, 2012, vol. 55, # 12, p. 5901 - 5921
[3] Patent: WO2006/38006, 2006, A2, . Location in patent: Page/Page column 26-27
[4] Patent: WO2009/116067, 2009, A2, . Location in patent: Page/Page column 139
  • 2
  • [ 163271-06-5 ]
  • [ 24424-99-5 ]
  • [ 343788-69-2 ]
YieldReaction ConditionsOperation in experiment
95%
Stage #1: With hydrogen; acetic acid In methanol at 20℃;
Description 4.; tert-Butyl 4-a rboxylate (D4); To a solution of 1-benzyl-4-methylpiperidin-4-amine (D3, 4.5g, 22mmol) in MeOH (20 ml) was added AcOH (1.32g, 22mmol) and Pd(OH)2-C (cat.) at room temperature, then a solution of di-tert-butyl dicarbonate (4.8Og, 22mmol) in methanol (20ml) was added to the mixture dropwise at room temperature. The mixture was stirred overnight under 50psi hydrogen pressure, then filtered and the methanol removed under vacuum. The residue was diluted with water (20ml) and washed with ethyl acetate (30ml). The water phase was adjusted to pH>12 with aqueous ammonia and extracted with dichloromethane (100ml). The extract was dried, filtered and concentrated to give the title compound (3.5g, 95percent) as yellow oil. 1H NMR (CDCI3) δ: 1.11 (3H, s), 1.30-1.50 (13H, m), 1.70-2.01 (2H, b), 3.35-3.38 (4H, m).
Reference: [1] Patent: WO2008/119718, 2008, A1, . Location in patent: Page/Page column 45
  • 3
  • [ 872850-48-1 ]
  • [ 343788-69-2 ]
YieldReaction ConditionsOperation in experiment
100% With water; potassium hydroxide In tetrahydrofuran at 20℃; for 18 h; Method Y: tert-butyl 4-amino-4-methylpiperidine-1-carboxylate
A mixture of potassium hydroxide (400 mg, 7 mmol) and tert-butyl 4-isocyanato-4-methylpiperidine-1-carboxylate (560 mg, 2.3 mmol) in tetrahydrofuran (4 ml) and water (4 ml) was stirred at room temperature for 18 hours.
The amine was extracted with ethyl acetate.
The organic phase was washed with brine, dried over magnesium sulfate and concentrated in vacuo to afford the desired compound (500 mg, quantitative yield).
1H NMR (CDCl3, 400 MHz) δ 1.17 (3H, s), 1.36-1.56 (4H, m), 1.47 (9H, s), 3.38-3.52 (4H, m).
Reference: [1] Patent: US2010/137305, 2010, A1, . Location in patent: Page/Page column 37
[2] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 14, p. 3675 - 3678
[3] Patent: WO2006/1752, 2006, A1, . Location in patent: Page/Page column 87
  • 4
  • [ 343788-67-0 ]
  • [ 343788-69-2 ]
YieldReaction ConditionsOperation in experiment
69% With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; potassium hydroxide In acetonitrile 10334] Compound 3 (26 g, 107 mmol) was dissolved with CR3CN (200 mE) and 2N KOR (100 mE). Then 1,3-di- bromo-5,5-dimethylimidazolidine-2,4-dione (15 g, 54 mmol) was added to the reaction and stirred overnight. Then the reaction pH was adjusted to 5 with 2N HC1 and extracted with EA to remove the impurity. The aqueous phase was adjusted to a pH of 10. The precipitate was collected to afford the desired product as a white solid (16 g, 69percent).
69% With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; potassium hydroxide In acetonitrile Step 3: Dissolved the compound 3 (26g, 107 mmol) in acetonitrile (200 ml) and 5N KOH (100 ml). Then added l,3-dibromo-5,5-dimethylimidazolidine-2,4-dione (15g, 54 mmol) into the system. The mixture was stirred overnight. Concentrated to remove acetonitrile, adjusted the pH of the water phase to 5 with 2N HC1 while cooling the water phase in ice bath, extracted with EA and collected the organic layer. Then, the pH of water phase was adjusted to 10, and a white precipitate formed. The white solid as compound 4 was isolated by filtration (16 g, 69percent).
69% With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; potassium hydroxide In acetonitrile Compound 3 (26 g, 107 mmoi) was dissolved with ACN (acetonitrile) (200 ml) and 5N KOH (10() ml). i,3-dibronio5,5dimethyhmidazohdine2.4dione (15 g,54nunol) was then added into the system. The mixture was stined overnight and concentrated to remove the ACN. The pH of the water phase was adjusted to about 5 with 2N HC1 in an ice bath, extracted with EA and separated. The p1-I of water phase was ihen adjusted to 10. The precipitate was collected to yield compound 4 as a white solid (16 g, 69percent).
Reference: [1] Patent: US2015/105384, 2015, A1, . Location in patent: Paragraph 0333; 0334
[2] Patent: WO2016/57779, 2016, A2, . Location in patent: Page/Page column 73; 74
[3] Patent: WO2016/94824, 2016, A1, . Location in patent: Page/Page column 34; 35; 43
[4] Organic Process Research and Development, 2009, vol. 13, # 6, p. 1145 - 1155
  • 5
  • [ 189321-63-9 ]
  • [ 343788-69-2 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 14, p. 3675 - 3678
[2] Patent: US2007/167442, 2007, A1, . Location in patent: Page/Page column 48
[3] Journal of Medicinal Chemistry, 2012, vol. 55, # 12, p. 5901 - 5921
  • 6
  • [ 3612-20-2 ]
  • [ 343788-69-2 ]
Reference: [1] Patent: WO2008/119718, 2008, A1,
  • 7
  • [ 3970-66-9 ]
  • [ 343788-69-2 ]
Reference: [1] Patent: WO2008/119718, 2008, A1,
  • 8
  • [ 155928-37-3 ]
  • [ 343788-69-2 ]
Reference: [1] Patent: WO2008/119718, 2008, A1,
  • 9
  • [ 91419-52-2 ]
  • [ 343788-69-2 ]
Reference: [1] Patent: US2015/105384, 2015, A1,
[2] Patent: WO2016/57779, 2016, A2,
[3] Patent: WO2016/94824, 2016, A1,
  • 10
  • [ 530115-96-9 ]
  • [ 343788-69-2 ]
Reference: [1] Patent: US2015/105384, 2015, A1,
[2] Patent: WO2016/57779, 2016, A2,
[3] Patent: WO2016/94824, 2016, A1,
  • 11
  • [ 142851-03-4 ]
  • [ 343788-69-2 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 14, p. 3675 - 3678
  • 12
  • [ 189442-87-3 ]
  • [ 343788-69-2 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 14, p. 3675 - 3678
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