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[ CAS No. 36476-88-7 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 36476-88-7
Chemical Structure| 36476-88-7
Chemical Structure| 36476-88-7
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Product Details of [ 36476-88-7 ]

CAS No. :36476-88-7 MDL No. :MFCD03093388
Formula : C17H20N2 Boiling Point : -
Linear Structure Formula :- InChI Key :KISVATOISQDZJU-UHFFFAOYSA-N
M.W : 252.35 Pubchem ID :10037874
Synonyms :

Calculated chemistry of [ 36476-88-7 ]

Physicochemical Properties

Num. heavy atoms : 19
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.29
Num. rotatable bonds : 4
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 82.53
TPSA : 29.26 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) : -6.04 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.73
Log Po/w (XLOGP3) : 2.54
Log Po/w (WLOGP) : 1.96
Log Po/w (MLOGP) : 2.77
Log Po/w (SILICOS-IT) : 2.92
Consensus Log Po/w : 2.58

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.21
Solubility : 0.156 mg/ml ; 0.000619 mol/l
Class : Soluble
Log S (Ali) : -2.8
Solubility : 0.399 mg/ml ; 0.00158 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.95
Solubility : 0.00284 mg/ml ; 0.0000112 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 1.65

Safety of [ 36476-88-7 ]

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 [ 36476-88-7 ]

* 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 [ 36476-88-7 ]

[ 36476-88-7 ] Synthesis Path-Downstream   1~14

  • 1
  • [ 36476-88-7 ]
  • [ 407-25-0 ]
  • 1-(diphenylmethyl)-3-(((trifluoroacetyl)amino)methyl)azetidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
In chloroform for 2h; Ambient temperature;
  • 2
  • [ 36476-88-7 ]
  • 3-(aminomethyl)azetidine dihydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; hydrogen In methanol
  • 3
  • [ 36476-86-5 ]
  • [ 36476-88-7 ]
YieldReaction ConditionsOperation in experiment
With lithium aluminium tetrahydride
With lithium aluminium tetrahydride In tetrahydrofuran Ambient temperature;
In tetrahydrofuran; ethanol 23.A (1-Diphenylmethylazetidin-3-ylmethyl)-amine Example 23A (1-Diphenylmethylazetidin-3-ylmethyl)-amine A solution of 10 g (40 mmol) 1-diphenylmethylazetidin-3-carbonitrile in 20 ml abs. THF are added dropwise at RT to a suspension of 3.1 g (80 mmol) lithium aluminum hydride in 80 ml abs. THF and stirred overnight, 2 ml ethanol are carefully added to the batch and the batch is filtered. The filtrate is concentrated under vacuum and dispersed between CHCl3 and water. The aqueous phase is extracted twice, each with 50 ml CHCl3, and the combined organic phases are dried over sodium sulfate and the solvent is removed under vacuum. The residue is chromatographically purified over silica gel with CHCl3/CH3OH/NH4OH (90/10/0 to 90/10/1). Yield: 5.6 g (57%) of slowly solidifying resin.
Stage #1: 1-(1,1-diphenylmethyl)azetidine-3-carbonitrile With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 0.666667h; Heating / reflux; Stage #2: With sodium hydroxide; water In tetrahydrofuran at 0℃; for 0.333333h; 111 [Referential Example 111]; (1-Benzhydrylazetidin-3-yl)-N,N-dimethylmethylamine; [] 1-Benzhydrylazetidine-3-carbonitrile (880 mg) in tetrahydrofuran (10 mL) was added dropwise to a suspension of lithium aluminum hydride (134 mg) in tetrahydrofuran (20 mL) at 0°C, and the resultant mixture was refluxed under heat for 40 minutes. Under cooling at 0°C, to the reaction mixture, water (134 µl) and 15% aqueous sodium hydroxide (134 µl) were added dropwise, and then water (387 µl) was added thereto, followed by stirring for 20 minutes. The reaction mixture was filtered, and the filtrate was partitioned between water and ethyl acetate. The aqueous layer was extracted with ethyl acetate. The organic layers were combined, and washed twice with saturated brine, and then dried over sodium sulfate anhydrate, followed by filtration. The solvent was evaporated under reduced pressure. Methanol (20 mL) was added to the residue. To the mixture, sodium cyanoborohydride (1.11 g) and 37% aqueous formaldehyde (1.48 mL) were added at room temperature, followed by stirring for 24 hours. The solvent was evaporated under reduced pressure, and the residue was partitioned between water and chloroform. The aqueous layer was extracted with chloroform. The organic layers were combined, and sequentially washed with saturated aqueous sodium hydrogencarbonate and saturated brine, and then dried over sodium sulfate anhydrate, followed by filtration. The solvent was evaporated under reduced pressure, and the residue was purified through silica gel column chromatography (chloroform - methanol), to thereby give the title compound as an oily product (161 mg, 16%).1H-NMR(400MHz,CDCl3)δ: 2.16(6H,s), 2.45(2H,d,J=6.8Hz), 2.67(1H,m), 2.74(2H,t,J=7.6Hz), 3.39(2H,t,J=7.6Hz), 4.32(1H,s), 7.14-7.18(2H,m), 7.23-7.27(4H,m), 7.38(4H,dd,J=1.5,8.3Hz). LC-MSm/z: 281(M+H)+.

YieldReaction ConditionsOperation in experiment
10, Pd(OH)2*C/H2, LiAlH4;
23 3-Aminomethyl N-diphenylmethyl azetidine, (34) EXAMPLE 23 STR25 3-Aminomethyl N-diphenylmethyl azetidine, (34) To a cooled solution of aluminum chloride (0.33 g, 2.41 mmol) in ether (50 mL) at -78° C. was added lithium aluminum hydride (2.41 ml, 2.41 mmol). After stirring 15 minutes at -78° C. the slurry was added a solution of 33 (0.50 g, 2.01 mmol) in ether (10 mL) dropwise. The resulting mixture was stirred at room temperature for 2 hours. The solution was cooled to 0° C. and quenched with water (10 mL) dropwise followed by 25% NaOH solution (10 mL). The aqueous layer was extracted with EtOAc. The organics were dried over Na2 SO4, filtered, and removed in vacuo. The crude product was not purified. 1 H NMR (CDCl3, 300 MHz) 7.41-7.13 (m, 10H), 4.32 (s, 1H), 3.28 (t, 2H), 2.88-2.79 (m, 4H), 2.52-2.42(m, 1H), 1.28 (s, 1H).
V 1-(Diphenylmethyl)-3-azetidinemethanamine EXAMPLE V 1-(Diphenylmethyl)-3-azetidinemethanamine A suspension of 5.7 g (0.15 mole) of lithium aluminum hydride in 200 ml of dry tetrahydrofuran was treated portionwise with 18.6 g (75 mmole) of solid 3-cyano-1-(diphenylmethyl)azetidine. When the addition was complete, the reaction was stirred at room temperature for two hours, refluxed for four hours, and stirred at room temperature for 18 hours. The reaction was decomposed by the successive addition of 6 ml of water, 6 ml of 15% sodium hydroxide, and 18 ml of water, titrating the final water addition to give a granular precipitate. The inorganic precipitate was removed by filtration, washed with tetra hydrofuran and evaporated in vacuo to give 16.9 g of 1-(diphenylmethyl)-3-azetidinemethanamine as a heavy oil.
11 3-Aminomethyl N-diphenylmethyl azetidine, (16) EXAMPLE 11 3-Aminomethyl N-diphenylmethyl azetidine, (16) To a cooled solution of aluminum chloride (0.33 g, 2.41 mmol) in ether (50 mL) at -78° C. was added lithium aluminum hydride (2.41 ml, 2.41 mmol). After stirring 15 minutes at -78° C. the slurry was added a solution of 15 (0.50 g, 2.01 mmol) in ether (10 mL) dropwise. The resulting mixture was stirred at room temperature for 2 hours. The solution was cooled to 0° C. and quenched with water (10 mL) dropwise followed by 25% NaOH solution (10 mL). The aqueous layer was extracted with EtOAc. The organics were dried over Na2SO4, filtered, and removed in vacuo. The crude product was not purified. 1H NMR (CDCl3, 300 MHz) 7.41-7.13 (m, 10H), 4.32 (s, 1H), 3.28 (t, 2H), 2.88-2.79 (m, 4H), 2.52-2.42(m, 1H), 1.28 (s, 1H).

  • 5
  • [ 18621-17-5 ]
  • [ 36476-88-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: triethylamine / CH2Cl2 / Ambient temperature 2: dimethylformamide / 6 h / 65 °C 3: LiAlH4 / tetrahydrofuran / Ambient temperature
  • 6
  • [ 33301-41-6 ]
  • [ 36476-88-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: dimethylformamide / 6 h / 65 °C 2: LiAlH4 / tetrahydrofuran / Ambient temperature
  • 7
  • [ 50-00-0 ]
  • [ 36476-88-7 ]
  • [ 55438-74-9 ]
YieldReaction ConditionsOperation in experiment
With sodium cyanoborohydride In methanol; water at 20℃; for 24h; 111 [Referential Example 111]; (1-Benzhydrylazetidin-3-yl)-N,N-dimethylmethylamine ; [] 1-Benzhydrylazetidine-3-carbonitrile (880 mg) in tetrahydrofuran (10 mL) was added dropwise to a suspension of lithium aluminum hydride (134 mg) in tetrahydrofuran (20 mL) at 0°C, and the resultant mixture was refluxed under heat for 40 minutes. Under cooling at 0°C, to the reaction mixture, water (134 µl) and 15% aqueous sodium hydroxide (134 µl) were added dropwise, and then water (387 µl) was added thereto, followed by stirring for 20 minutes. The reaction mixture was filtered, and the filtrate was partitioned between water and ethyl acetate. The aqueous layer was extracted with ethyl acetate. The organic layers were combined, and washed twice with saturated brine, and then dried over sodium sulfate anhydrate, followed by filtration. The solvent was evaporated under reduced pressure. Methanol (20 mL) was added to the residue. To the mixture, sodium cyanoborohydride (1.11 g) and 37% aqueous formaldehyde (1.48 mL) were added at room temperature, followed by stirring for 24 hours. The solvent was evaporated under reduced pressure, and the residue was partitioned between water and chloroform. The aqueous layer was extracted with chloroform. The organic layers were combined, and sequentially washed with saturated aqueous sodium hydrogencarbonate and saturated brine, and then dried over sodium sulfate anhydrate, followed by filtration. The solvent was evaporated under reduced pressure, and the residue was purified through silica gel column chromatography (chloroform - methanol), to thereby give the title compound as an oily product (161 mg, 16%).1H-NMR(400MHz,CDCl3)δ: 2.16(6H,s), 2.45(2H,d,J=6.8Hz), 2.67(1H,m), 2.74(2H,t,J=7.6Hz), 3.39(2H,t,J=7.6Hz), 4.32(1H,s), 7.14-7.18(2H,m), 7.23-7.27(4H,m), 7.38(4H,dd,J=1.5,8.3Hz). LC-MSm/z: 281(M+H)+.
  • 8
  • [ 36476-88-7 ]
  • [ 321890-21-5 ]
YieldReaction ConditionsOperation in experiment
86% With formaldehyd; formic acid 35.b Azetidin-3-ylmethyldimethylamine, dihydrochloride b) A mixture of 3-(aminomethyl)-1(1,1-diphenyl methyl)azetidine (10.9 g, 43 mmol), formaldehyde (21.8 mL) and formic acid (21.8 mL) was stirred under reflux for one hour and then evaporated under reduced pressure. The resulting residue was mixed with ice, basified with aqueous sodium hydroxyde 2N and extracted with dichloromethane. The organic solution was washed with water, brine, dried (MgSO4) and evaporated under reduced pressure to yield [1-(1,1-diphenylmethyl)azetidin-3-ylmethyl]dimethylamine (10.4 g, 86%) as an oil. δ(CDCl3): 2.16 (6H, s), 2.44 (2H, d), 2.6-2.8 (4H, m), 3.38 (2H, t), 4.32 (1H, s), 7.1-7.3 (10 H, m).
  • 9
  • aqueous sodium hydroxyde [ No CAS ]
  • [ 36476-86-5 ]
  • [ 36476-88-7 ]
YieldReaction ConditionsOperation in experiment
73% In tetrahydrofuran; water 35.a Azetidin-3-ylmethyldimethylamine, dihydrochloride a) A solution of 1-(1,1-diphenylmethyl)azetidine-3-carbonitrile (7.8 g, 31.4 mmol) in 30 mL of tetrahydrofuran was slowly added to a suspension of lithium aluminium hydride (4.0 g, 105 mmol) in tetrahydrofuran under nitrogen and the resulting mixture was stirred under reflux for one hour. On cooling, the mixture was treated dropwise with water (4 mL), aqueous sodium hydroxyde (4 mL, 4N), and water (12 mL) and filtered. The filtrate was concentrated under reduced pressure to yield 3-(aminomethyl)-1-(1,1-diphenylmethyl)azetidine as a white solid (5.2 g, 73%).
  • 10
  • [ 36476-88-7 ]
  • [ 91189-19-4 ]
YieldReaction ConditionsOperation in experiment
24 3-N-(1,1-dimethylethoxycarbonyl)aminomethyl N-diphenylmethyl azetidine, (35) EXAMPLE 24 STR26 3-N-(1,1-dimethylethoxycarbonyl)aminomethyl N-diphenylmethyl azetidine, (35) The title compound was prepared from 34 using the procedure described for the preparation of 14. 1 H NMR (CDCl3, 300 MHz) 7.40-7.14 (m, 10H), 4.84 (s, 1H), 4.31 (s, 1H), 3.50-3.21 (m, 4H), 2.85 (t, 2H), 2.59-2.48 (m, 1H), 1.44 (s, 9H).
  • 11
  • [ 24424-99-5 ]
  • [ 36476-88-7 ]
  • 3-[bis-(tert-butoxycarbonylamino)methyl]-1-(diphenylmethyl)-azetidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine In tetrahydrofuran at 60℃; for 5h; Intermediate 152: 3-[i>w-(½rf-Butoxycarbonylamino)methyl]- l-(diphenylmethyl)-azetidine [00498] Di-tert-butyl dicarbonate (22g) was added to a solution of 1- (diphenylmethyl)azetidin-3-ylmethylamine (5g), DMAP (0.5g) and triethylamine (12g) in THF (150mL) and the resultant solution was stirred and heated at 60°C for 5 hours. After cooling, the mixture was added to brine solution and extracted with ethyl acetate, washed with brine, dried (Na2SC>4) and filtered. The filtrate was evaporated to dryness and the residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and petroleum ether (10%) to give 3-[i>w-(½rf-butoxycarbonylamino)methyl]-l-(diphenylmethyl)azetidine (6.4g) as a white solid, which was used without further characterisation.
  • 12
  • [ 24424-99-5 ]
  • [ 36476-88-7 ]
  • [ 1412978-13-2 ]
YieldReaction ConditionsOperation in experiment
6.4 g With dmap; triethylamine In tetrahydrofuran at 60℃; for 5h; 152 Intermediate 152: 3-[/?w-(tert-Butox carbonylamino)methyl]-l-(diphenylmethyl)-azetidine Intermediate 152: 3-[/?w-(tert-Butox carbonylamino)methyl]-l-(diphenylmethyl)-azetidine [00423] Di-tert-butyl dicarbonate (22g) was added to a solution of 1- (diphenylmethyl)azetidin-3-ylmethylamine (5g), DMAP (0.5g) and triethylamine (12g) in THF (150mL) and the resultant solution was stirred and heated at 60°C for 5 hours. After cooling, the mixture was added to brine solution and extracted with ethyl acetate, washed with brine, dried ( a2S04) and filtered. The filtrate was evaporated to dryness and the residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and petroleum ether (10%) to give 3-[/?-(ter?-butoxycarbonylamino)methyl]-l-(diphenylmethyl)azetidine (6.4g) as a white solid, which was used without further characterisation.
  • 13
  • [ 36476-88-7 ]
  • (3aS,4S,6R,6aR)-6-(4-[(2,4-dimethoxyphenyl)methyl]amino}-5-(1-methyl-1H-pyrazol-3-yl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-N-[1-(diphenylmethyl)azetidin-3-yl]methyl}-2,2-dimethyl-N-(1-methylpiperidin-4-yl)-tetrahydro-2H-furo[3,4-d][1,3]dioxole-4-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: methanol / 0.5 h / 20 °C 1.2: 20 h 2.1: N-ethyl-N,N-diisopropylamine; 2-chloro-1-methyl-pyridinium iodide / acetonitrile / 12 h / 80 °C
  • 14
  • [ 1445-73-4 ]
  • [ 36476-88-7 ]
  • N-[1-(diphenylmethyl)azetidin-3-yl]methyl}-1-methylpiperidin-4-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
43.6% Stage #1: 1-methylpiperidin-4-one; 3-(aminomethyl)-1-(1,1-diphenylmethyl)azetidine In methanol at 20℃; for 0.5h; Stage #2: With sodium cyanotrihydridoborate In methanol for 20h; 18.1 18.1 Synthesis of compound 3 1-[l-(Diphenylmethyl)azetidin-3-yl]methanamine (300 mg, 1.18 mmol), 1- methylpiperidin-4-one (267 mg, 2.36 mmol) were mixed in MeOH (5 mL).the mixture was stirred at rt for 30min. NaBH3CN (365 mg, 5.90 mmol) was added and stirred at for 20h. TLC show reaction completed. The reaction solution concentrated under reduced pressure to afford the crude. The crude was purified by TLC(MeOH/DCM=l/10) to afford the target compound ( 180 mg, yield 43.6 %). LC-MS m/z = 350.1 [M+H]+.
43.6% Stage #1: 1-methylpiperidin-4-one; 3-(aminomethyl)-1-(1,1-diphenylmethyl)azetidine In methanol at 20℃; for 0.5h; Stage #2: With sodium cyanotrihydridoborate In methanol for 20h; 18.1 18.1 Synthesis of compound 3 1-[l-(Diphenylmethyl)azetidin-3-yl]methanamine (300 mg, 1.18 mmol), 1- methylpiperidin-4-one (267 mg, 2.36 mmol) were mixed in MeOH (5 mL).the mixture was stirred at rt for 30min. NaBH3CN (365 mg, 5.90 mmol) was added and stirred at for 20h. TLC show reaction completed. The reaction solution concentrated under reduced pressure to afford the crude. The crude was purified by TLC(MeOH/DCM=l/10) to afford the target compound ( 180 mg, yield 43.6 %). LC-MS m/z = 350.1 [M+H]+.
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