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[ CAS No. 51207-85-3 ] {[proInfo.proName]}

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Chemical Structure| 51207-85-3
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Product Details of [ 51207-85-3 ]

CAS No. :51207-85-3 MDL No. :MFCD00461426
Formula : C11H16N2O Boiling Point : -
Linear Structure Formula :- InChI Key :RNVOPVJRSRXPSX-UHFFFAOYSA-N
M.W : 192.26 Pubchem ID :458760
Synonyms :

Calculated chemistry of [ 51207-85-3 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.36
Num. rotatable bonds : 4
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 58.36
TPSA : 46.33 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) : -7.02 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.96
Log Po/w (XLOGP3) : 0.64
Log Po/w (WLOGP) : 1.76
Log Po/w (MLOGP) : 1.83
Log Po/w (SILICOS-IT) : 1.27
Consensus Log Po/w : 1.49

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.49
Solubility : 6.25 mg/ml ; 0.0325 mol/l
Class : Very soluble
Log S (Ali) : -1.19
Solubility : 12.5 mg/ml ; 0.0648 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.91
Solubility : 0.237 mg/ml ; 0.00123 mol/l
Class : Soluble

Medicinal Chemistry

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

Safety of [ 51207-85-3 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501 UN#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 51207-85-3 ]

* 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 [ 51207-85-3 ]

[ 51207-85-3 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 5323-47-7 ]
  • [ 51207-85-3 ]
YieldReaction ConditionsOperation in experiment
93% With sodium tetrahydridoborate In tetrahydrofuran; lithium hydroxide monohydrate at 20℃; for 3h; Green chemistry;
87% With sodium tetrahydridoborate In ethanol; lithium hydroxide monohydrate at 20℃; for 4h; Green chemistry; 4.5 General procedure for the reduction of nitro aromatic using starch-crt(at)Au General procedure: To a flask containing nitroarene (0.5 mmol), starch-crt(at)Au (0.1 mol%, 25 mg) and NaBH4 (2.5 mmol, 45 mg), 2 mL of H2O:EtOH (1:1) was added. Reaction mixture was stirred at room temperature for the appropriate reaction times (see Tables 2 and 3). Progress of the reactions were monitored by GC, TLC and or 1H NMR. After completion of the reaction, the crude product was extracted with ethyl acetate (3 × 5 mL). The solvent was evaporated and the residue was purified using column or plate chromatography.
85% With palladium 10% on activated carbon; hydrogen In methanol; dichloromethane at 20℃;
83% With palladium 10% on activated carbon; ammsnium formate In methanol for 1h; Cooling with ice; E Preparation E4-(N ,N -diethylcarboxamido )aniline [0059] Ammonium formate (20.0 g, 317 mmol) was added to a vigorously stirred mixture ofN,N-diethyl4-nitrobenzamide (20.0 g, 90 mmol) and 1.0 g of 10% palladium/charcoal in400 mL of methanol cooled on ice. The reaction warms with vigorous gas evolution. After 1 h,TLC ( 60/40 hexane/EtOAc) indicated complete conversion of the starting material. The mixture was filtered through a pad of Celite and evaporated to a crystalline solid. This wassuspended in water and collected by vacuum filtration. The product was recrystallized fromwater and dried to provide 14.14 g (83%) of white crystals. 1H-NMR (400 MHz, CDCb): 87.22 (2H, m), 6.65 (2H, m), 3.81 (2H, br s), 3.42 (4H, br s), 1.17 (6H, t, J = 6.8 Hz).
80% With hydrazine hydrate monohydrate In ethanol for 4h; Heating;
78.2% With iron(0); ammonia hydrochloride In methanol; lithium hydroxide monohydrate at 70℃;
75% With hydrogen; C45H56BN5OPRh(2+)*2F6Sb(1-) In toluene at 60℃; for 15h; Glovebox; chemoselective reaction;
With hydrogenchloride; glacial acetic acid; stannous chloride
With ammsnium formate In methanol at 20℃; for 2h; 28.2 A mixture of N,N-diethyl 4- nitrobenzamide (4.44 g) and 10% palladium on carbon (0.2 g) in 100 mL of methanol was treated with ammonium formate (4.0 g) for 2 h at ambient temperature. The mixture was filtered through diatomaceous earth and concentrated. The residue was redissolved in DCM, washed successively with 0.5 M Na2C03, water, and brine, then dried over MgS04, filtered, and evaporated to provide a crystalline material. Recrystallization from ethyl acetate/hexane provided the product aniline.
With palladium 10% on activated carbon; ammsnium formate In methanol at 20℃; for 2h; 12.2 (2) 4-(N,N-diethylcarboxamido)aniline: A mixture of N,N-diethyl 4- nitrobenzamide (4.44 g) and 10% palladium on carbon (0.2 g) in 100 mL of methanol was treated with ammonium formate (4.0 g) for 2 h at ambient temperature. The mixture was filtered through Celite and concentrated. The residue was redissolved in DCM, washed successively with 0.5 M Na2C03, water, and brine, then dried over MgS04, filtered, and evaporated to provide a crystalline material. Recrystallization from ethyl acetate/hexane provided the product aniline. [0086] Also prepared according to the same procedure was 4-(morpholinocarbonyl)aniline by replacing diethylamine with morpholine.
With palladium 10% on activated carbon; ammsnium formate In methanol at 20℃; for 2h; 12.2 2) 4-(N,N-diethylcarboxamido)aniline (2) 4-(N,N-diethylcarboxamido)aniline: A mixture of N,N-diethyl 4-nitrobenzamide (4.44 g) and 10% palladium on carbon (0.2 g) in 100 mL of methanol was treated with ammonium formate (4.0 g) for 2 h at ambient temperature. The mixture was filtered through Celite and concentrated. The residue was redissolved in DCM, washed successively with 0.5 M Na2C03, water, and brine, then dried over MgS04, filtered, and evaporated to provide a crystalline material. Recrystallization from ethyl acetate/hexane provided the product aniline.
With palladium 10% on activated carbon; hydrogen In methanol; dichloromethane for 12.5h;
With palladium 10% on activated carbon; ammsnium formate In methanol at 20℃; for 2h; 12 Preparation of 4-(N,N-Diethylcarboxamido)Aniline (2) 4-(N,N-diethylcarboxamido)aniline A mixture of N,N-diethyl 4-nitrobenzamide (4.44 g) and 10% palladium on carbon (0.2 g) in 100 mL of methanol was treated with ammonium formate (4.0 g) for 2 h at ambient temperature. The mixture was filtered through Celite and concentrated. The residue was redissolved in DCM, washed successively with 0.5 M Na2CO3, water, and brine, then dried over MgSO4, filtered, and evaporated to provide a crystalline material. Recrystallization from ethyl acetate/hexane provided the product aniline.
90 %Chromat. With sodium tetrahydridoborate In ethanol; lithium hydroxide monohydrate at 20℃; for 1.5h;

Reference: [1]Gholinejad, Mohammad; Oftadeh, Erfan; Shojafar, Mohammad; Sansano, José M.; Lipshutz, Bruce H. [ChemSusChem, 2019, vol. 12, # 18, p. 4240 - 4248]
[2]Gholinejad, Mohammad; Dasvarz, Neda; Shojafar, Mohammad; Sansano, José M. [Inorganica Chimica Acta, 2019, vol. 495]
[3]Chiba, Mayumi; Ichikawa, Yuki; Kamiya, Mako; Komatsu, Toru; Ueno, Tasuku; Hanaoka, Kenjiro; Nagano, Tetsuo; Lange, Norbert; Urano, Yasuteru [Angewandte Chemie - International Edition, 2017, vol. 56, # 35, p. 10418 - 10422][Angew. Chem., 2017, vol. 129, # 35, p. 10554 - 10558]
[4]Current Patent Assignee: PROLYNX - WO2015/51307, 2015, A1 Location in patent: Paragraph 0059
[5]Srivastava, Neera; Gupta, Anurag Ateet; Gupta, Anil K. Sen [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1982, vol. 21, p. 787 - 789]
[6]Li, Xinyu; Shi, Binyu; Teng, Yu; Cheng, Yu; Yang, Huizhu; Li, Jiurong; Wang, Lianjian; He, Siying; You, Qidong; Xiang, Hua [MedChemComm, 2019, vol. 10, # 2, p. 294 - 299]
[7]Chugh, Vishal; Chatterjee, Basujit; Chang, Wei-Chieh; Cramer, Hanna H.; Hindemith, Carsten; Randel, Helena; Weyhermüller, Thomas; Farès, Christophe; Werlé, Christophe [Angewandte Chemie - International Edition, 2022, vol. 61, # 36][Angew. Chem., 2022, vol. 134, # 36]
[8]Wenker [Journal of the American Chemical Society, 1938, vol. 60, p. 1081]
[9]Current Patent Assignee: PROLYNX - WO2011/140393, 2011, A1 Location in patent: Page/Page column 44
[10]Current Patent Assignee: PROLYNX - WO2013/36857, 2013, A1 Location in patent: Paragraph 0085
[11]Current Patent Assignee: PROLYNX - WO2013/36847, 2013, A1 Location in patent: Paragraph 0114
[12]Piao, Wen; Hanaoka, Kenjiro; Fujisawa, Tomotsumi; Takeuchi, Satoshi; Komatsu, Toru; Ueno, Tasuku; Terai, Takuya; Tahara, Tahei; Nagano, Tetsuo; Urano, Yasuteru [Journal of the American Chemical Society, 2017, vol. 139, # 39, p. 13713 - 13719]
[13]Current Patent Assignee: PROLYNX - US2017/312368, 2017, A1 Location in patent: Paragraph 01
[14]Khosravi, Faezeh; Gholinejad, Mohammad; Sansano, José M.; Luque, Rafael [Applied Organometallic Chemistry, 2022, vol. 36, # 7]
  • 2
  • [ 50-00-0 ]
  • [ 536-17-4 ]
  • [ 51207-85-3 ]
  • [ 104183-56-4 ]
YieldReaction ConditionsOperation in experiment
81% In ethanol; water Heating;
  • 3
  • [ 5892-99-9 ]
  • [ 51207-85-3 ]
YieldReaction ConditionsOperation in experiment
99% With tris(dibenzylideneacetone)dipalladium (0); lithium hexamethyldisilazane; CyJohnPhos In 1,4-dioxane at 80℃; for 15h;
94% With dicyclohexyl(2',4',6'-triisopropyl-5-methoxy-3,4,6-trimethyl-[1,1'-biphenyl]-2-yl)phosphine; C50H70NO4PPdS; C50H70NO4PPdS; dicyclohexyl(2',4',6'-triisopropyl-4-methoxy-3,5,6-trimethyl-[1,1'-biphenyl]-2-yl)phosphine; ammonia; sodium t-butanolate In 1,4-dioxane at 20℃; for 36h; Inert atmosphere;
  • 4
  • [ 1336-21-6 ]
  • Ti(Oi-Pr)4 [ No CAS ]
  • [ 775-16-6 ]
  • [ 51207-85-3 ]
  • [ 209902-32-9 ]
YieldReaction ConditionsOperation in experiment
44% With sodium tetrahydroborate; In ethanol; n-heptane; ethyl acetate; (i) Preparation of 4-[N-(1-benzyl-pyrrolidin-3-yl)-amino]-N,N-diethyl benzamide (compound 19) STR30 Ti(Oi-Pr)4 (3.1 ml, 10.4 mmol) was added to a mixture of 4-amino-(N,N-diethyl) benzamide (0.50 g, 2.51 mmol) and 1-benzyl-3-pyrrolidone (0.85 mL, 5.30 mmol) at room temperature. The mixture was sonicated at 40 C. for 3 h, and stirred at room temperature for 16 h. The mixture was cooled in an ice-bath and EtOH (30 mL) and NaBH4 (0.30 g, 8.00 mmol) were added. After stirring for 16 h at room temperature, 2M NH4 OH (20 mL) was added. The mixture was stirred at room temperature for 30 min, diluted with CH2 Cl2 (20 mL) and filtered through a pad of Celite. The layers in the filtrate were separated, the aqueous layer extracted with CH2 Cl2 (3*20 mL). The combined organic phases were washed with 10% HCl (2*20 mL). The pH in the combined aqueous extracts was adjusted to 10 with 2N NaOH, and extracted with CH2 Cl2 (3*20 mL). The combined organic extracts were dried over Na2 SO4, filtered, concentrated and the residue purified by chromatography (gradient, 9:1:0.5 to 9:0:1 EtOAc/heptane/Et3 N) to give the title compound 19 (0.40 g, 44%) as a pale yellow viscous oil. IR (neat): 3322, 1609, 1527, 1455 cm-1. 1 H NMR (CDCl3): 7.40-7.10 (7H, m), 6.60-6.40 (2H, m), 4.20 (1H, m), 3.95 (1H, m), 3.55 (2H, s), 3.35 (4H, bs), 2.70 (2H, m), 2.50-2.35 (2H, m), 2.25 (1H, m), 1.60 (1H, m), 1.15 (6H, bt). 13 C NMR (CDCl3): 171.4, 148.2, 138.4, 128.5, 128.2, 128.1, 126.7, 126.1, 113.8, 112.1, 60.5, 59.9, 52.5, 51.9, 41 (b), 32.2, 13.3.
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