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[ CAS No. 73391-96-5 ] {[proInfo.proName]}

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Chemical Structure| 73391-96-5
Chemical Structure| 73391-96-5
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Product Details of [ 73391-96-5 ]

CAS No. :73391-96-5 MDL No. :MFCD02751705
Formula : C10H12BrNO Boiling Point : -
Linear Structure Formula :- InChI Key :XIBVVIAYYYFAAI-UHFFFAOYSA-N
M.W : 242.11 Pubchem ID :150681
Synonyms :

Calculated chemistry of [ 73391-96-5 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.3
Num. rotatable bonds : 4
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 56.8
TPSA : 20.31 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.35 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.11
Log Po/w (XLOGP3) : 2.01
Log Po/w (WLOGP) : 1.89
Log Po/w (MLOGP) : 2.31
Log Po/w (SILICOS-IT) : 2.17
Consensus Log Po/w : 2.1

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.68
Solubility : 0.5 mg/ml ; 0.00207 mol/l
Class : Soluble
Log S (Ali) : -2.06
Solubility : 2.09 mg/ml ; 0.00864 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.74
Solubility : 0.0443 mg/ml ; 0.000183 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.34

Safety of [ 73391-96-5 ]

Signal Word:Danger Class:8
Precautionary Statements:P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P310-P332+P313-P362-P403+P233-P405-P501 UN#:3265
Hazard Statements:H315-H318-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 73391-96-5 ]

* 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 [ 73391-96-5 ]

[ 73391-96-5 ] Synthesis Path-Downstream   1~40

  • 1
  • [ 73391-96-5 ]
  • [ 294-90-6 ]
  • [ 132930-14-4 ]
YieldReaction ConditionsOperation in experiment
30% With potassium carbonate In N,N-dimethyl-formamide at 50℃; for 24h;
  • 2
  • [ 73391-96-5 ]
  • [ 178739-07-6 ]
  • (2R,3R,4S)-4-Benzo[1,3]dioxol-5-yl-1-[(benzyl-methyl-carbamoyl)-methyl]-2-(4-methoxy-phenyl)-pyrrolidine-3-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide; N-ethyl-N,N-diisopropylamine 1.) CH3CN, 50 deg C, 1 h, 2.) C2H5OH, RT, 3 h; Yield given. Multistep reaction;
  • 3
  • [ 4383-22-6 ]
  • [ 73391-96-5 ]
  • 2-(allylbenzylamino)-N-benzyl-N-methylacetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With triethylamine In tetrahydrofuran at 20℃; for 20h;
  • 4
  • [ 73391-96-5 ]
  • N,3-dibenzyl-N-methyl-3-azabicyclo[3.1.0]hex-1-ylamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 85 percent / Et3N / tetrahydrofuran / 20 h / 20 °C 2: 56 percent / methyltitanium triisopropoxide; cyclohexylmagnesium bromide / diethyl ether; tetrahydrofuran / 12 h / 20 °C
  • 5
  • [ 73391-96-5 ]
  • [ 132930-10-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 30 percent / potassium carbonate / dimethylformamide / 24 h / 50 °C 2: 16 percent / potassium carbonate / dimethylformamide / 10 h / 60 °C 3: 15 percent / tetramethylammonium hydroxide / methanol; H2O / 6 h / 100 °C
  • 6
  • [ 73391-96-5 ]
  • [ 132930-15-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 30 percent / potassium carbonate / dimethylformamide / 24 h / 50 °C 2: 16 percent / potassium carbonate / dimethylformamide / 10 h / 60 °C
  • 7
  • [ 1337537-34-4 ]
  • [ 73391-96-5 ]
  • [ 1337537-45-7 ]
YieldReaction ConditionsOperation in experiment
62% Stage #1: 4-methyl-2-phenyl-1H-pyrazolo[3,4-b]quinolin-3(2H)-one With sodium carbonate In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: N-methyl-N-(phenylmethyl)-2-bromoacetamide In N,N-dimethyl-formamide at 20℃;
  • 8
  • [ 598-21-0 ]
  • [ 103-67-3 ]
  • [ 73391-96-5 ]
YieldReaction ConditionsOperation in experiment
89% In dichloromethane at 0 - 20℃; for 1h;
76% In dichloromethane at 0 - 20℃; for 1h; Inert atmosphere;
72% In acetonitrile at 0 - 20℃; for 1h;
With sodium hydrogencarbonate In dichloromethane at 0 - 20℃; for 6h; Inert atmosphere; Synthesis of N-benzyl-N-methyl diazoacetamide (2a) Using the procedure of Fukuyama,1 N-methyl-benzylamine (605.4 mg, 5.0 mmol) and NaHCO3 (1266.1 mg, 15.0 mmol) were dissolved in CH2Cl2 (10.0 mL) and bromoacetyl bromide (976 μL, 10.0 mmol) was added slowly at 0 °C and stirred for 6 hours at room temperature, the reaction was quenched with H2O (50 mL) and the solution was extracted with CH2Cl2 (100 mL) three times. After washed with water and dried over Na2SO4, the solvent was evaporated and the residue was used in the next step without purification. The resulting bromoacetamide and N,N'-ditosylhydrazine (1036.0 mg, 3.04 mmol) were dissolved in THF (10.0 mL) and cooled down to 0 C, then DBU (1158.2 mg, 7.60 mmol) was added drop wise and stirred at room temperature for 1 h. After quenched with NaHCO3 aq and extracted with diethyl ether three times, the organic phase was dried over Na2SO4 and evaporated to give crude product. Purification was performed with flash column chromatography on silica gel eluted with hexane:EtOAc = 5:1 to give N-benzyl-N-methyl-diazoacetamide (242.0 mg, 69% yield in two steps) as a yellow oil. Rf = 0.5 (hexane:EtOAc = 1:1). 1H NMR (300 MHzCDCl3) δ 7.38-7.16 (m, 5H), 4.99 (s, 1H), 4.48 (br s, 2H), 2.84 (br s, 3H) ppm. 13C NMR (75 MHzCDCl3) δ 166.3, 137.2, 128.9, 127.7, 127.6 , 52.1, 46.6, 34.5 ppm. IR (NaCl, cm-1) 3739, 3088, 2920, 2361, 2104, 1749. EA Anal. Calcd. for C10H11N3O×0.1CH2Cl2×0.1CH3CO2CH2CH3: C 61.07, H 5.86, N 20.35%; Found C 61.44, H 5.79, N 20.72%.
With triethylamine In dichloromethane at 20℃; Inert atmosphere; Synthesis of 18, 22, 23, and 24 General procedure: Toa chilled solution (ice/water) of Benzylamine or N-Benzylmethylamine andTriethylamine(1.2 equiv.) in dry CH2Cl2 (5 mL/gbenzylamine)was added Bromoacetyl bromide (1.2equiv.) The reaction was allowed to warm to ambient temperature and monitoredby GC/MS. Upon consumption of the starting amine, The reaction was diluted with5 vol CH2Cl2 and washed 3x 5vol H2O. The aqueouslayer was back extracted 3x1 vol. The combined organics were dried over Na2SO4.The crude material was concentrated and subjected to the next reaction. Whennecessary, purification via flash chromatography was employed Toa chilled solution solution of the α-Bromoamide in acetonitrile (5 vol) wasadded 4 equiv. of benzylamine or N-benzylmethylamine. The reactions weremonitored by GC/MS. Upon completion, the reactions were diluted with 7.15 vol ethylacetate, washed 3x7.15 vol H2O, and 1x4vol saturated aqueous NaClsolution. Finally, the organics weredried over Na2SO4, decanted, concentrated en vacuo, and purified by flashchromatography
In dichloromethane at 0 - 20℃; for 24h;
With triethylamine In dichloromethane at 0 - 20℃; for 4h; Schlenk technique; Inert atmosphere;
With potassium carbonate In dichloromethane at 0 - 20℃; for 0.5h; Inert atmosphere;
With triethylamine In dichloromethane at 0 - 20℃; for 4h;
With triethylamine In acetonitrile at 20℃; for 3h;

Reference: [1]Cappelli, Andrea; Bini, Giulia; Valenti, Salvatore; Giuliani, Germano; Paolino, Marco; Anzini, Maurizio; Vomero, Salvatore; Giorgi, Gianluca; Giordani, Antonio; Stasi, Luigi Piero; Makovec, Francesco; Ghelardini, Carla; Di Cesare Mannelli, Lorenzo; Concas, Alessandra; Porcu, Patrizia; Biggio, Giovanni [Journal of Medicinal Chemistry, 2011, vol. 54, # 20, p. 7165 - 7175]
[2]Fetzer, Christian; Korotkov, Vadim S.; Sieber, Stephan A. [Organic and Biomolecular Chemistry, 2019, vol. 17, # 30, p. 7124 - 7127]
[3]Samanta, Sanjay; Lim, Ting Liang; Lam, Yulin [ChemMedChem, 2013, vol. 8, # 6, p. 994 - 1001]
[4]Chanthamath, Soda; Thongjareun, Songkharm; Shibatomi, Kazutaka; Iwasa, Seiji [Tetrahedron Letters, 2012, vol. 53, # 36, p. 4862 - 4865]
[5]Mitra, Aurpon W.; Hansen, Marvin M.; Laurila, Michael E.; Kolis, Stanley P.; Martinelli, Joseph R. [Tetrahedron Letters, 2013, vol. 54, # 48, p. 6580 - 6583]
[6]Wiȩckowska, Anna; Wichur, Tomasz; Godyń, Justyna; Bucki, Adam; Marcinkowska, Monika; Siwek, Agata; Wiȩckowski, Krzysztof; Zarȩba, Paula; Knez, Damijan; Głuch-Lutwin, Monika; Kazek, Grzegorz; Latacz, Gniewomir; Mika, Kamil; Kołaczkowski, Marcin; Korabecny, Jan; Soukup, Ondrej; Benkova, Marketa; Kieć-Kononowicz, Katarzyna; Gobec, Stanislav; Malawska, Barbara [ACS Chemical Neuroscience, 2018, vol. 9, # 5, p. 1195 - 1214]
[7]Zhou, Zijun; Chen, Shuming; Qin, Jie; Nie, Xin; Zheng, Xingwen; Harms, Klaus; Riedel, Radostan; Houk; Meggers, Eric [Angewandte Chemie - International Edition, 2019, vol. 58, # 4, p. 1088 - 1093][Angew. Chem., 2019, vol. 131, # 4, p. 1100 - 1105,6]
[8]Phan Thi Thanh, Nga; Tone, Masaya; Inoue, Hayato; Fujisawa, Ikuhide; Iwasa, Seiji [Chemical Communications, 2019, vol. 55, # 89, p. 13398 - 13401]
[9]Abularrage, Nile S.; Gold, Brian; Khanal, Namrata; Raines, Ronald T.; Dones, Jesús M. [Journal of the American Chemical Society, 2021, vol. 143, # 25, p. 9489 - 9497]
[10]Fallica, Antonino N.; Sorrenti, Valeria; D’Amico, Agata G.; Salerno, Loredana; Romeo, Giuseppe; Intagliata, Sebastiano; Consoli, Valeria; Floresta, Giuseppe; Rescifina, Antonio; D’Agata, Velia; Vanella, Luca; Pittalà, Valeria [Journal of Medicinal Chemistry, 2021, vol. 64, # 18, p. 13373 - 13393]
  • 9
  • [ 73391-96-5 ]
  • [ 122-52-1 ]
  • [ 883231-60-5 ]
YieldReaction ConditionsOperation in experiment
98% With sodium iodide In N,N-dimethyl-formamide for 0.025h; Microwave irradiation;
  • 10
  • [ 73391-96-5 ]
  • [ 1394816-74-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N,N'-ditosylhydrazine; 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 1 h / 0 - 20 °C / Inert atmosphere 2: [(4,5-dihydro-4,4-dimethyl-2-phenyloxazole)Ru(CH3CN)4]PF6 / dichloromethane / 0.08 h / 20 °C / Inert atmosphere
  • 11
  • [ 73391-96-5 ]
  • [ 1394816-76-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N,N'-ditosylhydrazine; 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 1 h / 0 - 20 °C / Inert atmosphere 2: [(4,5-dihydro-4,4-dimethyl-2-phenyloxazole)Ru(CH3CN)4]PF6 / dichloromethane / 0.08 h / 20 °C / Inert atmosphere
  • 12
  • [ 73391-96-5 ]
  • [ 1394816-77-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N,N'-ditosylhydrazine; 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 1 h / 0 - 20 °C / Inert atmosphere 2: [(4,5-dihydro-4,4-dimethyl-2-phenyloxazole)Ru(CH3CN)4]PF6 / dichloromethane / 0.08 h / 20 °C / Inert atmosphere
  • 13
  • [ 73391-96-5 ]
  • [ 1394816-78-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N,N'-ditosylhydrazine; 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 1 h / 0 - 20 °C / Inert atmosphere 2: [(4,5-dihydro-4,4-dimethyl-2-phenyloxazole)Ru(CH3CN)4]PF6 / dichloromethane / 0.08 h / 20 °C / Inert atmosphere
  • 14
  • [ 73391-96-5 ]
  • [ 1394816-79-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N,N'-ditosylhydrazine; 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 1 h / 0 - 20 °C / Inert atmosphere 2: [(4,5-dihydro-4,4-dimethyl-2-phenyloxazole)Ru(CH3CN)4]PF6 / dichloromethane / 0.08 h / 20 °C / Inert atmosphere
  • 15
  • [ 73391-96-5 ]
  • [ 1394816-80-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N,N'-ditosylhydrazine; 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 1 h / 0 - 20 °C / Inert atmosphere 2: [(4,5-dihydro-4,4-dimethyl-2-phenyloxazole)Ru(CH3CN)4]PF6 / dichloromethane / 0.08 h / 20 °C / Inert atmosphere
  • 16
  • [ 73391-96-5 ]
  • [ 1394816-81-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N,N'-ditosylhydrazine; 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 1 h / 0 - 20 °C / Inert atmosphere 2: [(4,5-dihydro-4,4-dimethyl-2-phenyloxazole)Ru(CH3CN)4]PF6 / dichloromethane / 0.08 h / 20 °C / Inert atmosphere
  • 17
  • [ 73391-96-5 ]
  • [ 1394816-82-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N,N'-ditosylhydrazine; 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 1 h / 0 - 20 °C / Inert atmosphere 2: [(4,5-dihydro-4,4-dimethyl-2-phenyloxazole)Ru(CH3CN)4]PF6 / dichloromethane / 0.08 h / 20 °C / Inert atmosphere
  • 18
  • [ 73391-96-5 ]
  • [ 1181671-91-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N,N'-ditosylhydrazine; 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 1 h / 0 - 20 °C / Inert atmosphere 2: [(4,5-dihydro-4,4-dimethyl-2-phenyloxazole)Ru(CH3CN)4]PF6 / dichloromethane / 1 h / 20 °C / Inert atmosphere
  • 19
  • [ 73391-96-5 ]
  • N-benzyl-2-diazo-N-methylacetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
242 mg With N,N'-ditosylhydrazine; 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran at 0 - 20℃; for 1h; Inert atmosphere; Synthesis of N-benzyl-N-methyl diazoacetamide (2a) Using the procedure of Fukuyama,1 N-methyl-benzylamine (605.4 mg, 5.0 mmol) and NaHCO3 (1266.1 mg, 15.0 mmol) were dissolved in CH2Cl2 (10.0 mL) and bromoacetyl bromide (976 μL, 10.0 mmol) was added slowly at 0 °C and stirred for 6 hours at room temperature, the reaction was quenched with H2O (50 mL) and the solution was extracted with CH2Cl2 (100 mL) three times. After washed with water and dried over Na2SO4, the solvent was evaporated and the residue was used in the next step without purification. The resulting bromoacetamide and N,N'-ditosylhydrazine (1036.0 mg, 3.04 mmol) were dissolved in THF (10.0 mL) and cooled down to 0 C, then DBU (1158.2 mg, 7.60 mmol) was added drop wise and stirred at room temperature for 1 h. After quenched with NaHCO3 aq and extracted with diethyl ether three times, the organic phase was dried over Na2SO4 and evaporated to give crude product. Purification was performed with flash column chromatography on silica gel eluted with hexane:EtOAc = 5:1 to give N-benzyl-N-methyl-diazoacetamide (242.0 mg, 69% yield in two steps) as a yellow oil. Rf = 0.5 (hexane:EtOAc = 1:1). 1H NMR (300 MHzCDCl3) δ 7.38-7.16 (m, 5H), 4.99 (s, 1H), 4.48 (br s, 2H), 2.84 (br s, 3H) ppm. 13C NMR (75 MHzCDCl3) δ 166.3, 137.2, 128.9, 127.7, 127.6 , 52.1, 46.6, 34.5 ppm. IR (NaCl, cm-1) 3739, 3088, 2920, 2361, 2104, 1749. EA Anal. Calcd. for C10H11N3O×0.1CH2Cl2×0.1CH3CO2CH2CH3: C 61.07, H 5.86, N 20.35%; Found C 61.44, H 5.79, N 20.72%.
With N,N'-ditosylhydrazine; 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran at 0℃; for 0.5h; Inert atmosphere;
Multi-step reaction with 2 steps 1: sodium azide / N,N-dimethyl-formamide / 20 °C 2: 3-(diphenylphosphaneyl)propanoic acid N-hydroxysuccinimide ether / water; tetrahydrofuran / 4 h / 20 °C
  • 20
  • [ 73391-96-5 ]
  • N-benzyl-2-(6-(2-bromoacetamido)benzo[d]thiazol-2-ylthio)-N-methylacetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium hydroxide / ethanol; water / 1 h / 20 °C 2: dichloromethane / 1 h / 0 - 20 °C
  • 21
  • [ 73391-96-5 ]
  • N-benzyl-N-methyl-2-(6-(2-(5-phenyl-4H-1,2,4-triazol-3-ylthio)acetamido)benzo[d]thiazol-2-ylthio)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: potassium hydroxide / ethanol; water / 1 h / 20 °C 2: dichloromethane / 1 h / 0 - 20 °C 3: potassium hydroxide / ethanol; water / 2 h / 20 °C
  • 22
  • [ 7442-07-1 ]
  • [ 73391-96-5 ]
  • C17H17N3OS2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium hydroxide In ethanol; water at 20℃; for 1h;
  • 23
  • [ 73391-96-5 ]
  • [ 100-46-9 ]
  • C17H20N2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
59% In acetonitrile Inert atmosphere; Synthesis of 18, 22, 23, and 24 General procedure: Toa chilled solution (ice/water) of Benzylamine or N-Benzylmethylamine andTriethylamine(1.2 equiv.) in dry CH2Cl2 (5 mL/gbenzylamine)was added Bromoacetyl bromide (1.2equiv.) The reaction was allowed to warm to ambient temperature and monitoredby GC/MS. Upon consumption of the starting amine, The reaction was diluted with5 vol CH2Cl2 and washed 3x 5vol H2O. The aqueouslayer was back extracted 3x1 vol. The combined organics were dried over Na2SO4.The crude material was concentrated and subjected to the next reaction. Whennecessary, purification via flash chromatography was employed Toa chilled solution solution of the α-Bromoamide in acetonitrile (5 vol) wasadded 4 equiv. of benzylamine or N-benzylmethylamine. The reactions weremonitored by GC/MS. Upon completion, the reactions were diluted with 7.15 vol ethylacetate, washed 3x7.15 vol H2O, and 1x4vol saturated aqueous NaClsolution. Finally, the organics weredried over Na2SO4, decanted, concentrated en vacuo, and purified by flashchromatography
  • 24
  • [ 73391-96-5 ]
  • [ 103-67-3 ]
  • C18H22N2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% In acetonitrile Inert atmosphere; Synthesis of 18, 22, 23, and 24 General procedure: Toa chilled solution (ice/water) of Benzylamine or N-Benzylmethylamine andTriethylamine(1.2 equiv.) in dry CH2Cl2 (5 mL/gbenzylamine)was added Bromoacetyl bromide (1.2equiv.) The reaction was allowed to warm to ambient temperature and monitoredby GC/MS. Upon consumption of the starting amine, The reaction was diluted with5 vol CH2Cl2 and washed 3x 5vol H2O. The aqueouslayer was back extracted 3x1 vol. The combined organics were dried over Na2SO4.The crude material was concentrated and subjected to the next reaction. Whennecessary, purification via flash chromatography was employed Toa chilled solution solution of the α-Bromoamide in acetonitrile (5 vol) wasadded 4 equiv. of benzylamine or N-benzylmethylamine. The reactions weremonitored by GC/MS. Upon completion, the reactions were diluted with 7.15 vol ethylacetate, washed 3x7.15 vol H2O, and 1x4vol saturated aqueous NaClsolution. Finally, the organics weredried over Na2SO4, decanted, concentrated en vacuo, and purified by flashchromatography
  • 25
  • [ 73391-96-5 ]
  • C17H20N2O*C2H2O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: acetonitrile / Inert atmosphere 2: acetonitrile; tert-butyl methyl ether / Cooling with ice; Inert atmosphere
  • 26
  • 1-benzyl-4-(piperazin-1-yl)-1H-indole hydrochloride [ No CAS ]
  • [ 73391-96-5 ]
  • N-benzyl-2-(4-(1-benzyl-1H-indol-4-yl)piperazin-1-yl)-N-methylacetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
50% With potassium carbonate In acetonitrile at 0 - 20℃; for 24h;
  • 27
  • [ 73391-96-5 ]
  • N-benzyl-2-(4-(3-(benzyloxy)-2-methylphenyl)piperazin-1-yl)-N-methylethan-1-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate / acetonitrile / 24 h / 50 °C 2: lithium aluminium tetrahydride / tetrahydrofuran
  • 28
  • [ 73391-96-5 ]
  • N-benzyl-2-(4-(1-benzyl-1H-indol-4-yl)piperazin-1-yl)-N-methylethan-1-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate / acetonitrile / 24 h / 0 - 20 °C 2: lithium aluminium tetrahydride / tetrahydrofuran
  • 31
  • [ 73391-96-5 ]
  • C15H20N2O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium azide / N,N-dimethyl-formamide / 50 °C / Schlenk technique; Inert atmosphere 2: C44H56N8RuSi2(2+)*2F6P(1-) / 1,2-dichloro-benzene / 48 h / 95 °C / Schlenk technique; Inert atmosphere
  • 32
  • [ 57-41-0 ]
  • [ 73391-96-5 ]
  • 3-(2-(N-benzyl-N-methyl-amino)-2-oxo-ethyl)-5,5-diphenylimidazolidine-2,4-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
29% With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 3h; Inert atmosphere; regioselective reaction;
  • 33
  • [ 73391-96-5 ]
  • [ 89617-59-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N,N'-ditosylhydrazine; 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere 2: Ru-pheox / dichloromethane / 4 h / 20 °C / Inert atmosphere
  • 34
  • [ 5814-41-5 ]
  • [ 73391-96-5 ]
  • N-benzyl-N-methyl-2-(11-oxo-10,11-dihydro-5H-dibenzo[b,e][1,4]diazepin-5-yl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% Stage #1: 5,10-dihydro-11H-dibenzo[b,e][1,4]-diazepin-11-one With potassium <i>tert</i>-butylate In tetrahydrofuran at 0 - 20℃; for 0.5h; Inert atmosphere; Stage #2: N-methyl-N-(phenylmethyl)-2-bromoacetamide In tetrahydrofuran at 0 - 20℃; Inert atmosphere; 8. General procedure for the synthesis of 6a-6d General procedure: To a solution of 21 (50 mg, 0.238 mmol, 1.0 equiv.) in tetrahydrofuran(0.2 M) was added potassium tert-butoxide (40 mg,0.357 mmol, 1.5 equiv.) at 0 °C and stirred for 30 min at ambienttemperature. The reaction mixture was cooled to 0 °C and theappropriate alkylating agent (1.1 equiv.) was added dropwise. Thereaction mixture was warmed to ambient temperature and stirred for 8 h. The reaction mixture was quenched with water at 0 °C and then diluted with ethyl acetate (10 mL). The organic layer was collected and the aqueous layer was further extracted with ethyl acetate (2 x 5 mL). The combined organic extracts were thenwashed with brine (2 mL), dried over magnesium sulfate andconcentrated in vacuo. Purification by flash chromatography on silica gel column using ethyl acetate/hexane (1:1 v/v) furnished the desired dibenzodiazepine ligands.
  • 35
  • [ 73391-96-5 ]
  • [ 479234-83-8 ]
  • N-benzyl-N-methyl-2-(1-methyl-4,10-dihydrobenzo[b]pyrazolo[3,4-e][1,4]diazepin-5(1H)-yl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With triethylamine In tetrahydrofuran at 20℃; for 19h; Inert atmosphere; 6.1. General procedure for the synthesis of 5a-5d General procedure: To a solution of 16 (100 mg, 0.499 mmol, 1.0 equiv.) in tetrahydrofuran(1 mL) was added triethylamine (140 μL, 0.999 mmol, 2.0equiv.), followed by the dropwise addition of the appropriatealkylating agent (1.1 equiv.). The reaction mixture was stirred atambient temperature for 19 h. The reaction mixture was evaporatedto dryness and diluted with ethyl acetate (5 mL) and water(2 mL). The organic layer was collected, and the aqueous layer wasfurther extracted with ethyl acetate (2 x 5 mL). The combinedorganic extracts werewashed with aqueous hydrochloric acid (1 M,2 mL), followed by water (2 mL). The organic layer was dried overmagnesium sulfate and concentrated in vacuo. Purification by flashchromatography on silica gel column using methanol/dichloromethane(5:95 v/v) furnished the desired pyrazolobenzodiazepine ligands.
  • 36
  • C19H19N3O3S2 [ No CAS ]
  • [ 73391-96-5 ]
  • C29H30N4O4S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine In acetonitrile for 5h; Inert atmosphere; Reflux;
  • 37
  • C18H19N3O2S2 [ No CAS ]
  • [ 73391-96-5 ]
  • C28H30N4O3S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine In acetonitrile for 5h; Inert atmosphere; Reflux;
  • 38
  • [ 73391-96-5 ]
  • C25H22ClN5O [ No CAS ]
  • C25H22ClN5O [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium azide / N,N-dimethyl-formamide / 20 °C 2: dichloromethane / 20 °C
  • 39
  • [ 73391-96-5 ]
  • C25H21ClN4O [ No CAS ]
  • C25H21ClN4O [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: sodium azide / N,N-dimethyl-formamide / 20 °C 2: 3-(diphenylphosphaneyl)propanoic acid N-hydroxysuccinimide ether / water; tetrahydrofuran / 4 h / 20 °C 3: dichloromethane / 20 °C
  • 40
  • [ 288-32-4 ]
  • [ 73391-96-5 ]
  • N-benzyl-2-(1H-imidazol-1-yl)-N-methylacetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
27% With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 2h;
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