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[ CAS No. 86732-22-1 ] {[proInfo.proName]}

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Chemical Structure| 86732-22-1
Chemical Structure| 86732-22-1
Structure of 86732-22-1 * Storage: {[proInfo.prStorage]}
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Product Details of [ 86732-22-1 ]

CAS No. :86732-22-1 MDL No. :MFCD04115126
Formula : C13H18N2 Boiling Point : -
Linear Structure Formula :- InChI Key :AOBSJQWEYXEPBK-UHFFFAOYSA-N
M.W : 202.30 Pubchem ID :4454387
Synonyms :

Calculated chemistry of [ 86732-22-1 ]

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.54
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 69.55
TPSA : 15.27 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.55 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.41
Log Po/w (XLOGP3) : 1.39
Log Po/w (WLOGP) : 0.42
Log Po/w (MLOGP) : 2.02
Log Po/w (SILICOS-IT) : 2.06
Consensus Log Po/w : 1.66

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.13
Solubility : 1.49 mg/ml ; 0.00735 mol/l
Class : Soluble
Log S (Ali) : -1.31
Solubility : 9.81 mg/ml ; 0.0485 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -3.39
Solubility : 0.0817 mg/ml ; 0.000404 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.05

Safety of [ 86732-22-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 86732-22-1 ]

* 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 [ 86732-22-1 ]
  • Downstream synthetic route of [ 86732-22-1 ]

[ 86732-22-1 ] Synthesis Path-Upstream   1~9

  • 1
  • [ 848591-86-6 ]
  • [ 86732-22-1 ]
YieldReaction ConditionsOperation in experiment
99%
Stage #1: With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 5 h; Heating / reflux
Stage #2: With water; sodium sulfate In tetrahydrofuran at 0 - 20℃; for 16 h;
2-Benzyloctahydropyrrolo[3,4-c] pyrrole (or 3-benzyl-3,7- diazabicyclo [3.3.0] octane);The crude 5-benzyltetrahydropyrrolo[3,4-c]pyrrole-l,3-dione (4.9 g, 0.021 mol) was dissolved in cold (O0C) dry tetrahydrofuran (THF) (50 mL) under nitrogen, and lithium aluminum hydride (63 mL of 1 M in THF, 0.063 mol) was added drop-wise over 30 min to the continuously cooled solution. The resulting mixture was stirred at ambient temperature for 30 min and then warmed to reflux for 4 h. The mixture was then cooled to 0°C and quenched by the slow addition of excess solid sodium sulfate decahydrate. The mixture was warmed to ambient temperature and stirred for 16 h. The solids were filtered and the residue was washed with ethyl acetate (3 x 100 mL). The combined filtrates were concentrated to give 4.2 g (99percent yield) of a waxy solid (MS m/z 203 (M+H)).
66%
Stage #1: With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 40℃; for 1 h;
Stage #2: With (+)-potassium sodium tartrate; water In tetrahydrofuran at 0℃;
To a solution of 5-(phenylmethyl)tetrahydropyrrolo[3,4-c]pyrrole-1,3(2H,3a/-/)-dione (367 mg, 1.59 mmol) in THF (16 mL) at 0 C was added dropwise a solution of LAH (7.2 mL, 7.2 mmol, 1M in THF). The reaction warmed to 25C and was heated to 40 C for an additional 1 h. Upon cooling to 0C, the reaction was quenched by dropwise addition of a saturated solution of potassium sodium tartrate. The aqueous phase was extracted several times with DCM and the combined organic fractions were dried over Na2SO4, concentrated and purified by column chromatography (silica, 10percent MeOH in DCM (1percent NH4OH)) yielding the title compound as a yellow oil (212 mg, 66percent): LCMS (ES) m/e 203
61% With lithium aluminium tetrahydride In tetrahydrofuran at -5℃; for 4 h; Reflux To a suspension of 5-benzyltetrahydropyrrolo[3,4-c]pyrrole- l ,3(2H,3aH)-dione (3.88 g) in THF (80 mL) at -5 °C was added LiAlH4 ( 1.92 g) slowly. The reaction mixture was heated to reflux for 4h, and then quenched with water, the mixture was extracted with EtOAc. The organic phase was dried over anhydrous Na2S04 for 1 h and filtered. The filtrate was concentrated in vacuo and the residue was chromatographed with a silica gel column (eluting agent: 200:30: 1 (v/v) DCM/MeOH/NH3H20) to give the title compound as oil (2.07 g, 61.00 percent).
61% With lithium aluminium tetrahydride In tetrahydrofuran at -5℃; Reflux To a suspension of 5-benzyltetrahydropyrrolo[3,4-c]pyrrole-1,3(2H,3aH)-dione (3.88 g) in THF (80 mL) at −5° C. was added LiAlH4 (1.92 g) slowly. The reaction mixture was heated to reflux for 4 h, and then quenched with water, the mixture was extracted with EtOAc. The organic phase was dried over anhydrous Na2SO4 for 1 h and filtered. The filtrate was concentrated in vacuo and the residue was chromatographed with a silica gel column (eluting agent: 200:30:1 (v/v) DCM/MeOH/NH3H2O) to give the title compound as oil (2.07 g, 61.00percent).
19.2 g With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 8 h; Inert atmosphere; Reflux The crude compound 3 (30 g, 0.13 mol) was dissolved in dry tetrahydrofuran (THF) (500 mL) under nitrogen atmosphere, and then lithium aluminium hydride (14.8 g, 0.39 mol) was slowly added at 0°C over 30 min. The resulting mixture was stirred at ambient temperature for 30 min and then warmed to reflux for 7 h. The mixture was then cooled to 0 ºC and quenched by the slow addition of an excess of H2O/THF solution (1/10). The mixture was warmed to ambient temperature and stirred for 1 h. The solids were filtered and the residue was washed with ethyl acetate (3 x 150 mL). The combined filtrates were concentrated to give 27 g of a crude material. Purification of the crude compound 4 was successfully performed by column chromatography with EtOAc/hexene (3/1 + 10 percent TEA) as an eluent. 19.2 g (73 percent yield) of the pure material were obtained.

Reference: [1] Patent: WO2008/57938, 2008, A1, . Location in patent: Page/Page column 30
[2] Patent: WO2006/12396, 2006, A1, . Location in patent: Page/Page column 21; 34
[3] Patent: WO2013/71697, 2013, A1, . Location in patent: Paragraph 00248
[4] Patent: US2014/228361, 2014, A1, . Location in patent: Paragraph 0368-0369
[5] Patent: US2005/101602, 2005, A1, . Location in patent: Page/Page column 28
[6] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 23, p. 5439 - 5445
[7] Patent: WO2009/111550, 2009, A1, . Location in patent: Page/Page column 36-37
  • 2
  • [ 86732-32-3 ]
  • [ 86732-22-1 ]
YieldReaction ConditionsOperation in experiment
94%
Stage #1: With lithium aluminium tetrahydride In tetrahydrofuran for 5 h; Heating / reflux
Stage #2: With potassium hydroxide In water
Man legt 16 g (0.42 mol) Lithiumaluminiumhydrid in 350 ml absolutem Tetra- hydrofuran vor und tropft 38 g (0.165 mol) von Beispiel XXVII in 150 ml absolutem Tetrahydrofuran hinzu. Man erhitzt noch fuenf Stunden unter Rueckfluss, tropft je 16 ml Wasser, 16 percent ige Kalilauge und wieder Wasser hinzu, saugt die anorganischen Salze ab und kocht sie zweimal mit Tetrahydrofuran aus. Die Filtrate werden einge- engt und im Membranpumpenvakuum destilliert. Es werden 31.4 g (94 percent d. Th. ) des Produktes erhalten. Siedepunkt : [140°C/4] mbar
92%
Stage #1: With lithium aluminium tetrahydride In tetrahydrofuran; diethyl ether; dichloromethane at 0℃; for 1.5 h;
Stage #2: With sodium hydroxide In tetrahydrofuran; diethyl ether; dichloromethane; water
A solution of lithium aluminum hydride (15.0 mL, 1. 0 M solution in ether) was added dropwise to a solution of compound 2 (1. 15 g) in THF (50 mL) and dichloromethane (40 mL) at 0 °C. The reaction mixture was stirred an additional 1.5 hour at 0 °C and water (0.5 mL) was added followed by the addition of aqueous NaOH solution (0.5 mL, 20percent) and then water (1.5 mL). The resulting solids was filtered off and the filtrate was concentrated iii vacuo. The residue was purified by flash chromatography to provide the title compound 3 as a pale yellow oil (0.93 g, 92percent). LCMS: Rf: 0.368 min, M+H+ : 203.
Reference: [1] Patent: WO2003/106450, 2003, A1, . Location in patent: Page column 53
[2] Patent: WO2005/84667, 2005, A1, . Location in patent: Page/Page column 72
[3] Journal of Heterocyclic Chemistry, 1983, vol. 20, p. 321 - 329
  • 3
  • [ 1631-26-1 ]
  • [ 50893-53-3 ]
  • [ 7689-50-1 ]
  • [ 86732-22-1 ]
Reference: [1] Patent: US6355641, 2002, B1, . Location in patent: Page column 39
  • 4
  • [ 86731-90-0 ]
  • [ 86732-22-1 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1983, vol. 20, p. 321 - 329
  • 5
  • [ 86731-92-2 ]
  • [ 86732-22-1 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1983, vol. 20, p. 321 - 329
  • 6
  • [ 86732-04-9 ]
  • [ 86732-22-1 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1983, vol. 20, p. 321 - 329
  • 7
  • [ 86731-94-4 ]
  • [ 86732-22-1 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1983, vol. 20, p. 321 - 329
  • 8
  • [ 93102-05-7 ]
  • [ 86732-22-1 ]
Reference: [1] Patent: WO2013/71697, 2013, A1,
[2] Patent: US2014/228361, 2014, A1,
[3] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 23, p. 5439 - 5445
[4] Patent: WO2009/111550, 2009, A1,
  • 9
  • [ 86732-22-1 ]
  • [ 141449-85-6 ]
Reference: [1] Patent: WO2011/50198, 2011, A1,
[2] Patent: WO2012/145581, 2012, A1,
[3] Patent: WO2013/71697, 2013, A1,
[4] Patent: US2014/228361, 2014, A1,
[5] Patent: WO2009/111550, 2009, A1,
[6] Patent: WO2005/121145, 2005, A2,
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