Home Cart 0 Sign in  
X

[ CAS No. 128740-14-7 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
3d Animation Molecule Structure of 128740-14-7
Chemical Structure| 128740-14-7
Chemical Structure| 128740-14-7
Structure of 128740-14-7 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 128740-14-7 ]

Related Doc. of [ 128740-14-7 ]

Alternatived Products of [ 128740-14-7 ]

Product Details of [ 128740-14-7 ]

CAS No. :128740-14-7 MDL No. :MFCD06796542
Formula : C14H20N2 Boiling Point : -
Linear Structure Formula :- InChI Key :AFYZAHZKOFBVLE-UHFFFAOYSA-N
M.W : 216.32 Pubchem ID :11356376
Synonyms :

Calculated chemistry of [ 128740-14-7 ]

Physicochemical Properties

Num. heavy atoms : 16
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.57
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 74.36
TPSA : 15.27 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.26 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.73
Log Po/w (XLOGP3) : 1.91
Log Po/w (WLOGP) : 0.96
Log Po/w (MLOGP) : 2.28
Log Po/w (SILICOS-IT) : 2.29
Consensus Log Po/w : 2.03

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.53
Solubility : 0.638 mg/ml ; 0.00295 mol/l
Class : Soluble
Log S (Ali) : -1.85
Solubility : 3.03 mg/ml ; 0.014 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -3.67
Solubility : 0.0457 mg/ml ; 0.000211 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.32

Safety of [ 128740-14-7 ]

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 [ 128740-14-7 ]

* 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.

  • Downstream synthetic route of [ 128740-14-7 ]

[ 128740-14-7 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 128740-13-6 ]
  • [ 128740-14-7 ]
YieldReaction ConditionsOperation in experiment
97.4% With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 3h; Reflux; 6-benzyloctahydro-1H-pyrrolo[3,4-b]pyridine (6e) To a solution of compound 6d (3.5 g, 14.3 mmol) in THF (40 ml) was added LAH (2.7 g, 71.7 mmol) in portions at 0°C. Then the reaction was refluxed for 3hr. The reaction was quenched by water and NaOH. The mixture was filtered and the filtrate was concentrated and purified by silica gel chromatography (eluting with petroleum ether/EtOAc=10:1~1:2) to give compound 6e (3.0 g, yield: 97.4%). 1H NMR (400MHz, CHLOROFORM-d) δ= 7.34 -7.30 (m, 4H), 7.26 - 7.21 (m, 1H), 3.72 (d, J=15.2 Hz, 2H), 3.24 - 3.19 (m, 1H), 2.97(td, J=3.9, 12.8 Hz, 1H), 2.84 (dd, J=5.2, 9.8 Hz, 1H), 2.79 - 2.72 (m, 1H), 2.65 - 2.52(m, 3H), 2.24 - 2.14 (m, 1H), 1.69 - 1.63 (m, 2H), 1.56 - 1.36 (m, 2H)
95% With sodium tetrahydroborate; zinc(II) chloride In tetrahydrofuran at 0℃; for 15h; Reflux; 7 Example 7 To 500mL three reaction flask was added tetrahydrofuran 200mL, cooled to 0 ° C,7.6 g (0.2 mol) of sodium borohydride, 13.7 g (0.1 mol) of zinc chloride,24.4 g (0.1 mol) of 8-benzyl-7,9-dioxo-2,8-diazabicyclo [4.3.0] nonane,Then warmed to reflux, incubated for 15 hours, the reaction was completed, cooled to room temperature,The reaction solution was added to 100mL2N HCl solution, filtered to remove the solid, the filtrate was concentrated under reduced pressure,Then, 200 mL of toluene was added thereto and adjusted to pH 10 with 2N aqueous sodium hydroxide solution,Let stand, points to the water layer, toluene layer washed with deionized water 50mL once, with anhydrous sodium sulfate stirring and drying,Filtration, the filtrate was concentrated to dryness under reduced pressure,Then 20.5 g of 8-benzyl-2,8-diazabicyclo [4.3.0] nonane was obtained by distillation under reduced pressure (108-110 ° C / 0.1 mbar) with a yield of 95.0% and a purity of 99.5 %.
85% Stage #1: cis-8-benzyl-7,9-dioxo-2,8-diazabicyclo[4.3.0]-nonane In tetrahydrofuran at 0℃; for 2h; Stage #2: With sodium tetrahydroborate; magnesium chloride In tetrahydrofuran at 0 - 50℃; for 8h; 7 Preparation of 8-benzyl-2,8-diazabicyclo[4.3.0]nonane To 2000 ml three-necked flask were added 244 g of 6-benzyloctahydropyrrolo[3,4-b]pyridine-5,7-dione (1.0 mol), 600 ml of tetrahydrofuran, cooled to 0 °C with stirring, was added 121 g (3.2 moles), kept under stirring at 0 °C for 2 hours, then slowly added dropwise sodium borohydride-magnesium chloride (magnesium chloride 304 g, 3.2mol) tetrahydrofuran solution of 500 ml , dropwise addition, 2 hours maintaining 0-5 °C, then warmed to 40-50 °C for 6 hours, TLC (thin layer chromatography) thereaction is followed until the starting material 6-benzyloctahydropyrrolo[3,4-b]pyridine-5,7-dione disappears, cooled to room temperature, 200 ml of concentrated hydrochloric acid was added dropwise, stirring was continued for 1 hour, the filtrate wasconcentrated under reduced pressure, followed by addition of 500 ml of toluene and 500 ml of 20% aqueous sodium hydroxide solution, stirred for 0.5 hours, the toluene layer was washed three times with deionized water, dried over anhydrous sodium sulfate overnight, filtered, and the filtrate was concentrated to dryness, and then vacuum distillation to give a pale yellow liquid 183 g, 85% yield.
85% With 1,1,3,3-Tetramethyldisiloxane; tris(pentafluorophenyl)borate In 1,4-dioxane at 110℃; for 16h; Inert atmosphere; Schlenk technique; 14 General experimental procedures of tri(pentaflurophenyl)borane-catalyzed reduction of cyclicimides (1) General procedure: To the mixture of B(C6F5)3 (5.0mol%) and cyclic imides (1.0mmol) in dioxane, was added PhSiH3 (3.0mmol) slowly under an atmosphere of nitrogen. The reaction mixture was stirred and refluxed at 110°C under an atmosphere of nitrogen. After the imide was consumed completely (detected by TLC) the mixture was added with aqueous ammonia (15mL) and extracted with CH2Cl2 (10mL×3). The combined organic phase was dried over Na2SO4, after removing the solvent under vacuum, the residue was purified by column chromatography to give the product.
84.6% Stage #1: cis-8-benzyl-7,9-dioxo-2,8-diazabicyclo[4.3.0]-nonane With sodium tetrahydroborate; dimethyl sulfate In tetrahydrofuran at 5 - 30℃; for 18h; Stage #2: With hydrogenchloride; water In toluene at 80 - 85℃; for 1h; Stage #3: With sodium hydroxide In water at 5 - 10℃; 1 To a 250ml round bottom flask was charged sodium borohydride (9.3g) dissolved in tetrahydrofuran (80ml), the suspension formed was cooled to a temperature of 5°C to 10°C. Then to the reaction mixture dropwise added dimethyl sulphate (15.2g) and the reaction mixture was warmed to a temperature of 30°C and further stirred for 2 hours. The reaction mixture was then cooled to a temperature of 5°C to 10°C. A solution of compound of formula Ila (lOg) in tetrahydrofuran was added to the reaction mixture dropwise and the reaction mixture was then warmed to a temperature of 30°C. The reaction mixture further stirred for 18 hours at a temperature of 20°C to 30°C. The reaction solvent was distilled out and then charged toluene (50ml) to the reaction mixture. Further to the reaction mixture dropwise added concentrated hydrochloric acid (20ml) dissolved in water (40ml). The reaction mixture was stirred for another 1 hour and heated at a temperature of 80°C to 85°C. The reaction mixture was cooled at a temperature of 25°C to 30°C to precipitate the solid and the solid obtained was filtered. The filtrate obtained forms two layers, the aqueous layer was separated from the reaction mixture. The separated aqueous layer was then cooled to a temperature of 5°C to 10°C and the pH of the reaction mixture adjusted to 12 using sodium hydroxide solution. Then charged toluene (50ml) to the reaction mixture and stirred the reaction mixture for 15 min. The two layers formed were separated. The aqueous layer was extracted with toluene. All the organic layers were combined and washed with brine solution. The organic layer was dried over sodium sulphate and was evaporated to dryness to obtain the product.Yield = 84.6% Purity = 99.81%
70% With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 5℃; for 10h;
47% With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; Reflux; 25.2 6-benzyloctahydro-1H-pyrrolo[3,4-b]pyridine To a solution of LiAlH4 (1.20 g) in THF was added slowly 6-benzyltetrahydro-1H-pyrrolo[3,4-b]pyridine-5,7(6H,7aH)-dione (3.00 g) at 0° C. The reaction mixture was refluxed for 6 h under N2, and then cooled to rt. The reaction mixture was quenched with water at 0° C. and filtered. The filtrate was concentrated in vacuo and the residue was chromatographed with a silica gel column (eluting agent: 10:1 (v/v) EA/MeOH) to give the title compound as yellow oil (1.50 g, 47.00%), HPLC: 90.00%. The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 217.1 (M+1); 1H NMR (400 MHz, CDCl3) δ: 1.49-1.50 (m, 2H), 1.63-1.66 (m, 2H), 2.76-2.88 (m, 2H), 1.90 (s, 1H), 2.17-2.19 (m, 1H), 2.52-2.63 (m, 4H), 2.74 (t, J=10.4 Hz, 1H), 2.81-2.84 (m, 1H), 2.95-2.98 (m, 1H), 3.21-3.22 (m, J=4.0 Hz), 3.66 (q, J=12.6 Hz, 1H), 7.22-7.34 (m, 5H) ppm.
With ammonium hydroxide In tetrahydrofuran; water R.8 6-Benzyl-octahydropyrrolo[3.4-b]pyridine REFERENCE EXAMPLE 8 6-Benzyl-octahydropyrrolo[3.4-b]pyridine In 50 ml of anhydrous THF was suspended 4.9 g of lithium aluminum hydride, and a solution of 3 g of 6-benzyl -5,7-dioxo-octahydropyrrolo[3.4-b]pyridine in 50 ml of anhydrous THF was added thereto dropwise with stirring while cooling with ice. After the addition, the reaction mixture was heated under reflux for 6 hours. After completion of the reaction, 4.9 ml of water, 4.9 ml of aqueous ammonia, and 15 ml of water were added to the reaction mixture in this order while cooling with ice, followed by stirring for 30 minutes. The reaction mixture was filtered through Celite, and the filter cake was washed with THF (100 ml*4). The combined filtrate and washings were dried over anhydrous sodium sulfate and concentrated to yield 2.49 g of the titled compound as an oily substance. 1 H-NMR (400 MHz, CDCl3) δ ppm: 1.31-1.4 (2H, m), 1.46-1.65 (2H, m), 2.02 (1H, br s), 2.12-2.20 (1H, m), 2.47-2.54 (2H, m), 2.56 and 2.69 (each 1H, each t, J=8.8Hz), 2.78 (1H, dd, J=5.4, 10.3Hz), 2.91 (1H, dt, J=12.7, 3.9Hz), 3.15 (1H, dt, J=5.4, 2.0Hz), 3.63 and 3.69 (each 1H, each d, J=12.7Hz), 7.14-7.28 (5H, m)
With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 6h; Inert atmosphere; Reflux; 25.2 6-benzyloctahvdro-l H-pyrrolor3,4-blpyridine To a solution of L1AIH4 (1.20 g) in THF was added slowly 6-benzyltetrahydro-lH-pyrrolo[3,4-b]pyridine-5,7(6H,7aH)-dione (3.00 g) at 0°C. The reaction mixture was refluxed for 6 h under N2, and then cooled to rt. The reaction mixture was quenched with water at 0°C and filtered. The filtrate was concentrated in vacuo and the residue was chromatographed with a silica gel column (eluting agent: 10: 1 (v/v) EA/MeOH) to give the title compound as yellow oil ( 1.50 g, 47.00 %), HPLC: 90.00 %. The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 217.1 (M+1);'H NMR (400 MHz, CDC13) ?: 1.49-1.50 (m, 2H), 1.63-1.66 (m, 2H), 2.76-2.88 (m, 2H), 1.90 (s, 1 H), 2.17-2.19 (m, 1 H), 2.52-2.63 (m, 4H), 2.74 (t, J = 10.4 Hz, 1 H), 2.81 -2.84 (m, 1 H), 2.95-2.98 (m, 1 H), 3.21-3.22 (m, J = 4.0 Hz), 3.66 (q, J= 12.6 Hz, 1 H), 7.22-7.34 (m, 5H) ppm.

  • 2
  • [ 128740-13-6 ]
  • [ 128740-14-7 ]
YieldReaction ConditionsOperation in experiment
With sodium bis(2-methoxyethoxy)aluminium dihydride In toluene at 0 - 67℃; for 7.5h; 4 8-Benzyl-7,9-dione-2,8-diazabicyclo[4.30]nonane (62.45g,0.2559mole) as obtained from the Example 2 above was dissolved in toluene (125mL) at 5O0C, the reaction mixture was cooled to 0-50C followed by the addition of vitride (332.4g, 1.4518mole). To this reaction mixture was further added with the toluene solution for 2 hours. The reaction mixture was stirred for 30 minutes and the temperature was raised to 27-300C and maintained for 1 hour. The reaction mixture was further heated to 62-670C for 4 hours, cooled to room temperature and then to 0-50C followed by the addition of 20% sodium hydroxide solution. The reaction mixture was again heated to 550C, stirred for 30 minutes and the toluene layer was separated, washed with saturated sodium chloride solution and distilled off under vacuum below 60 ° C. Constant weight-52.61 gm
  • 3
  • [ 128740-14-7 ]
  • [ 151213-39-7 ]
YieldReaction ConditionsOperation in experiment
35% With D-tartaric acid In ethanol; N,N-dimethyl acetamide; isopropyl alcohol Resolution of racemate;
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 128740-14-7 ]

Aryls

Chemical Structure| 132414-50-7

[ 132414-50-7 ]

1-Benzyloctahydropyrrolo[3,4-b]pyrrole

Similarity: 0.98

Chemical Structure| 1354621-59-2

[ 1354621-59-2 ]

(3S,4S)-1-Benzyl-N,4-dimethylpiperidin-3-amine

Similarity: 0.95

Chemical Structure| 477600-69-4

[ 477600-69-4 ]

cis-1-Benzyl-N,4-dimethylpiperidin-3-amine

Similarity: 0.95

Chemical Structure| 1062580-52-2

[ 1062580-52-2 ]

(3R,4R)-1-Benzyl-N,4-dimethylpiperidin-3-amine dihydrochloride

Similarity: 0.93

Chemical Structure| 1235437-44-1

[ 1235437-44-1 ]

(R)-1-Benzyl-N,N-dimethylpyrrolidin-3-amine

Similarity: 0.88

Related Parent Nucleus of
[ 128740-14-7 ]

Aliphatic Heterocycles

Chemical Structure| 132414-50-7

[ 132414-50-7 ]

1-Benzyloctahydropyrrolo[3,4-b]pyrrole

Similarity: 0.98

Chemical Structure| 1354621-59-2

[ 1354621-59-2 ]

(3S,4S)-1-Benzyl-N,4-dimethylpiperidin-3-amine

Similarity: 0.95

Chemical Structure| 1062580-52-2

[ 1062580-52-2 ]

(3R,4R)-1-Benzyl-N,4-dimethylpiperidin-3-amine dihydrochloride

Similarity: 0.93

Chemical Structure| 1235437-44-1

[ 1235437-44-1 ]

(R)-1-Benzyl-N,N-dimethylpyrrolidin-3-amine

Similarity: 0.88

Chemical Structure| 114715-38-7

[ 114715-38-7 ]

(S)-1-Benzyl-3-aminopyrrolidine

Similarity: 0.86

Other Aliphatic Heterocycles

Chemical Structure| 132414-50-7

[ 132414-50-7 ]

1-Benzyloctahydropyrrolo[3,4-b]pyrrole

Similarity: 0.98

Chemical Structure| 116258-17-4

[ 116258-17-4 ]

(1S,4S)-2-Benzyl-2,5-diazabicyclo[2.2.1]heptane dihydrobromide

Similarity: 0.86

Chemical Structure| 76272-35-0

[ 76272-35-0 ]

endo-8-Benzyl-8-azabicyclo[3.2.1]octan-3-amine

Similarity: 0.86

Chemical Structure| 86732-22-1

[ 86732-22-1 ]

2-Benzyloctahydropyrrolo[3,4-c]pyrrole

Similarity: 0.81

Chemical Structure| N/A

[ N/A ]

((1R,5S,6R)-3-Benzyl-3-azabicyclo[3.1.0]hexan-6-yl)methanol

Similarity: 0.73