Home Cart 0 Sign in  

[ CAS No. 131885-34-2 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
Chemical Structure| 131885-34-2
Chemical Structure| 131885-34-2
Structure of 131885-34-2 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 131885-34-2 ]

Related Doc. of [ 131885-34-2 ]

Alternatived Products of [ 131885-34-2 ]

Product Details of [ 131885-34-2 ]

CAS No. :131885-34-2 MDL No. :MFCD17336280
Formula : C13H11FN2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :AEFSTURDBIFIBJ-UHFFFAOYSA-N
M.W : 246.24 Pubchem ID :14751679
Synonyms :

Calculated chemistry of [ 131885-34-2 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 18
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.08
Num. rotatable bonds : 4
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 69.01
TPSA : 57.85 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.05 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.34
Log Po/w (XLOGP3) : 3.88
Log Po/w (WLOGP) : 3.42
Log Po/w (MLOGP) : 3.37
Log Po/w (SILICOS-IT) : 1.28
Consensus Log Po/w : 2.86

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.04
Solubility : 0.0224 mg/ml ; 0.0000911 mol/l
Class : Moderately soluble
Log S (Ali) : -4.79
Solubility : 0.00397 mg/ml ; 0.0000161 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -5.04
Solubility : 0.00227 mg/ml ; 0.0000092 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 2.18

Safety of [ 131885-34-2 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P330-P363-P501 UN#:
Hazard Statements:H302-H312-H332 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 131885-34-2 ]

* 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 [ 131885-34-2 ]

[ 131885-34-2 ] Synthesis Path-Downstream   1~25

  • 1
  • [ 700-36-7 ]
  • [ 100-46-9 ]
  • [ 131885-34-2 ]
YieldReaction ConditionsOperation in experiment
86% Under Argon and at RT, Pd(OAc)2 (32 mg, 0.14 mmol) and BINAP (90 mg, 0.14 mmol) were added to a solution of benzylamine (225 mg, 2.10 mmol) and 4-fluoro-2-bromonitrobenzene (463 mg, 2.10 mmol) in toluene (degassed by purging, 5 mL). The reaction mixture was heated at 100 C. for 3 minutes and then cooled to 0 C. Upon addition of sodium tert-butoxide (253 mg, 2.63 mmol) the reaction mixture turned red. The reaction was stirred at 70 C. for 24 hours and then at RT for 48 hours. The reaction was filtered over Kiezelguhr. Residue was rinsed with EtOAc. The filtrate was evaporated to dryness in vacuo. The crude product was purified by flash column chromatography to afford N1-benzyl-5-fluoro-2-nitroaniline as a yellow crystalline compound (440 mg, 86%, purity (LC) n.d.).NMR: 1H (CDCl3): delta 8.55 (bs, 1H), 8.24 (dd, J=6.04 Hz and J=9.32 Hz, 1H), 7.42-7.30 (m, 5H), 6.46 (dd, J=2.52 Hz and J=11.4 Hz, 1H), 6.39 (ddd, J=2.52 Hz and J=7.32 Hz and J=9.60 Hz, 1H), 2.12 (s, 2H).
  • 2
  • [ 131885-34-2 ]
  • [ 760968-77-2 ]
  • [ 951666-39-0 ]
YieldReaction ConditionsOperation in experiment
Stage #1: benzyl-(5-fluoro-2-nitro-phenyl)-amine; methyl 5-hydroxy-2-(4-methylbenzenesulfonylamino)benzoate With potassium carbonate In N,N-dimethyl-formamide at 20 - 80℃; for 18h; Stage #2: With potassium hydrogensulfate In water; ethyl acetate; N,N-dimethyl-formamide A mixture of methyl 5-hydroxy-2-[(4-methylphenyl)sulfonyl]aminobenzoate (431 mg, 1.34 mmol), N1-benzyl-5-fluoro-2-nitroaniline (324 mg, 1.32 mmol), and potassium carbonate (365 mg, 2.64 mmol) in DMF (10 mL) was stirred at 80° C. for 6 hours and then at RT for 12 hours. The reaction was diluted with brine (150 mL) and was extracted with EtOAc (75 mL). The EtOAc-extract was washed with aq. 0.5 M KHSO4 (75 mL), aq. sat. NaHCO3 (75 mL), and brine (75 mL). The aqueous-layers were extracted with EtOAc (75 mL). The combined EtOAc-extracts were dried (Na2SO4), filtered, and evaporated to dryness in vacuo. The crude product was purified by column chromatography (EtOAc/heptane: 1/6 to 1/4) to obtain the desired product as a yellow solid (611 mg, 83%, purity (LC)=85%).MS: [M-H]-=546.
  • 3
  • [ 446-35-5 ]
  • [ 100-46-9 ]
  • [ 131885-34-2 ]
YieldReaction ConditionsOperation in experiment
95% With N-ethyl-N,N-diisopropylamine In 1,4-dioxane at 50℃; Benzyl-(5-fluoro-2-nitro-phenyl)-amine E-1.1" Benzyl-(5-fluoro-2-nitro-phenyl)-amine E-1.1" 2,4-Difluoronitrobenzene E-1.1'" (3.448 ml; 31.429 mmol) is dissolved in dioxane (35.000 ml). DIPEA (6.601 ml; 40.857 mmol) and benzylamine (3.429 ml; 31.429 mmol) are added. The reaction mixture is stirred at 50° C. overnight. The reaction mixture is concentrated under reduced pressure. The residue crystallises after some minutes. It is triturated with diethyl ether to give the pure crystalline compound. Yield: 95% (7.36 g; 28.890 mmol) HPLC-MS: (M+H)+=247; tRet=1.37 min; method LCMS BAS1
95% With N-ethyl-N,N-diisopropylamine In 1,4-dioxane at 50℃; 1 Benzyl-(5-fluoro-2-nitro-phenyl)-amine E- 1.1” Benzyl-(5-fluoro-2-nitro-phenyl)-amine E- 1.1” 2,4-Difluoronitrobenzene E-1.1” (3.448 ml; 3 1.429 mmol) is dissolved in dioxane (35.000 ml). DIPEA (6.601 ml; 40.857 mmol) and benzylamine (3.429 ml; 31.429mmol) are added. The reaction mixture is stirred at 50°C overnight. The reaction mixture is concentrated under reduced pressure. The residue crystallises after some minutes. It is triturated with diethyl ether to give the pure crystalline compound. Yield: 95% (7.36 g; 28.890 mmol)HPLC-MS: (M+H)+ = 247; tRet = 1.37 mm; method LCMS BAS1
85% Stage #1: benzylamine With potassium carbonate at 50℃; for 0.25h; Inert atmosphere; Stage #2: 2,4-Difluoronitrobenzene at 50℃; for 3h; 98 N-benzyl-5-fluoro-2-nitroaniline (LW) To a stiiied solution of benzyl amine (1,38 mL, 12.87 mmol) in Toluene (20 mL) under argon atmosphere was added potassium carbonate (868 nig,. 6.28 mmol) at RT. The reaction mixture was stirred at 50 V'C for 15 rain. Then 2, 4-difhioro- i -nitrobenzene (LV; 2 g, 12.57 mmol) was added to the reaction mixture at 50 °C stirred for 3 h. The progress of the reaction was monitored by TLC. The reaction mixture was diluted with ice cold water (100 mL) to obtain the solid. The solid was filtered, dissolved in CC (50 mL), dried over anhydrous MaiSC^ and concentrated under reduced pressure. The crude material was purified by silica gel column chromatography (eluen 2% EtOAc/Hexane) to afford compound L W (2.6 g. 10.56 mmol, 85%) as a brown solid. 1HNMR (400 MHz. CDC13): 5 8.57 (brs, IH), 8.27 (dd, J= 9.5. 6. Hz, iH), 7.49-7.31 (m, 5H), 6.49 (dd, J = 11.4, 2.6 Hz, IH), 6.51-6.4] (m, IH). 4.53 (d, J= 5.6 Hz, 2H).
99.2 %Chromat. With potassium carbonate In toluene at 45 - 50℃; regioselective reaction;
With triethylamine In dimethyl sulfoxide at 20℃; for 16h;
With potassium carbonate In N,N-dimethyl-formamide at 50℃; Example: 5-fluoro-N-(3-morpholinopropyl)-2-nitroaniline (5a) General procedure: The synthetic pathways for the preparation of compounds 6e-g are depicted in Scheme S2. In a 25 mL round bottom flask, compound 3 (159 mg, 1 mmol) and 3-morpholinopropan-1-amine (4a, 144mg, 1mmol) were dissolved in DMF (10 mL) and heated to 50 °C for overnight. After completion of the reaction, the reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed three times with saturated aqueous NaCl, and dried over anhydrous Na2SO4. And then, product by column chromatography purification. 5-fluoro-N-(3-morpholinopropyl)-2-nitroaniline (5a), yield 56%.
1.5 g With N-ethyl-N,N-diisopropylamine In dimethyl sulfoxide Cooling with ice; Inert atmosphere; In a 150 mL flask with a magnetic stirring bar, 2,4-difluoronitrobenzene (1.0 g, 6.29 mmol) and DIPEA (1.6 g,12.58 mmol) were suspended in 10 mL DMSO and cooled in icewaterbath, then benzyl amine (0.67 g, 6.29 mmol) was added tothe reaction mixture. After stirring overnight, the reaction mixturewas quenched by 100 mL NaHCO3 saturated solution. The yellowprecipitate was collected by filtration and washed by 50 mL waterthree times and 50 mL hexane twice. After drying by high vacuum,1.5 g of yellow solid was generated.

  • 4
  • [ 131885-34-2 ]
  • N3-benzyl-4-nitro-benzene-1,3-diamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
84% With ammonia In tetrahydrofuran at -70 - 90℃; for 17h; N3-benzyl-4-nitro-benzene-1,3-diamine E-1.5" N3-benzyl-4-nitro-benzene-1,3-diamine E-1.5" Ammonia (49 mmol) is purged in THF for 1 h at -70° C., benzyl-(5-fluoro-2-nitro-phenyl)-amine E-1.1" (6.000 g; 24 mmol) is added to the reaction mixture. The reaction mixture is stirred in a steel bomb vessel at 90° C. for 16 h. The reaction is then cooled to 0° C., diluted with water and extracted with ethyl acetate. The combined organic layers are dried with Na2SO4, filtered and concentrated under reduced pressure. The residue is used in the next step without further purification (yield: 84%; 5.000 g; 20.554 mmol).
84% With ammonia In tetrahydrofuran at 90℃; for 16h; 2 N3-benzyl-4-nitro-benzene- 1 ,3-diamine E- 1.5” N3-benzyl-4-nitro-benzene- 1 ,3-diamine E- 1.5” Ammonia (49 mmol) is purged in THF for 1 h at -70°C, benzyl-(5-fluoro-2-nitro-phenyl)-amine E-1.1” (6.000 g; 24 mmol) is added to the reaction mixture. Thereaction mixture is stirred in a steel bomb vessel at 90°C for 16 h. The reaction is then cooled to 0°C, diluted with water and extracted with ethyl acetate. The combined organic layers are dried with Na2SO4, filtered and concentrated under reduced pressure. The residue is used in the next step without further purification(yield: 84%; 5.000 g; 20.554 mmol).
  • 5
  • [ 131885-34-2 ]
  • (3-benzylamino-4-nitro-phenyl)-carbamic acid tert-butyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: ammonia / tetrahydrofuran / 17 h / -70 - 90 °C 2.1: triethylamine / dichloromethane / 0.17 h / 0 °C 2.2: 20 °C
Multi-step reaction with 2 steps 1.1: ammonia / tetrahydrofuran / 16 h / 90 °C 2.1: triethylamine / dichloromethane / 0.17 h / 0 °C 2.2: 20 °C
  • 6
  • [ 131885-34-2 ]
  • 5-[1-benzyl-6-(4-methylpiperazin-1-yl)-1H-1,3-benzodiazol-2-yl]-1,3-dimethyl-1,2-dihydropyridin-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: acetonitrile / 0.67 h / 160 °C 2: hydrogen / tetrahydrofuran / 20 °C / 375.04 - 4500.45 Torr / Autoclave 3: 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine / tetrahydrofuran / 5 h / 20 °C 4: acetic acid / 80 °C
Multi-step reaction with 4 steps 1: acetonitrile / 0.67 h / 160 °C / Microwave irradiation 2: hydrogen / tetrahydrofuran / 21 h / 20 °C / 375.04 - 4500.45 Torr / Autoclave 3: triethylamine; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide / tetrahydrofuran / 5 h / 20 °C 4: acetic acid / 80 °C
  • 7
  • [ 131885-34-2 ]
  • 1,5-dimethyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid [2-benzylamino-4-(4-methyl-piperazin-1-yl)-phenyl]-amide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: acetonitrile / 0.67 h / 160 °C / Microwave irradiation 2: hydrogen / tetrahydrofuran / 21 h / 20 °C / 375.04 - 4500.45 Torr / Autoclave 3: triethylamine; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide / tetrahydrofuran / 5 h / 20 °C
Multi-step reaction with 3 steps 1: acetonitrile / 0.67 h / 160 °C 2: hydrogen / tetrahydrofuran / 20 °C / 375.04 - 4500.45 Torr / Autoclave 3: 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine / tetrahydrofuran / 5 h / 20 °C
  • 8
  • [ 131885-34-2 ]
  • N2-benzyl-4-(4-methyl-piperazin-1-yl)-benzene-1,2-diamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: acetonitrile / 0.67 h / 160 °C / Microwave irradiation 2: hydrogen / tetrahydrofuran / 21 h / 20 °C / 375.04 - 4500.45 Torr / Autoclave
Multi-step reaction with 2 steps 1: acetonitrile / 0.67 h / 160 °C 2: hydrogen / tetrahydrofuran / 20 °C / 375.04 - 4500.45 Torr / Autoclave
  • 9
  • [ 131885-34-2 ]
  • 5-(6-amino-1-benzyl-1H-benzoimidazol-2-yl)-1,3-dimethyl-1H-pyridin-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: ammonia / tetrahydrofuran / 17 h / -70 - 90 °C 2.1: triethylamine / dichloromethane / 0.17 h / 0 °C 2.2: 20 °C 3.1: ammonium chloride / water; ethanol / 0.33 h / 70 °C 3.2: 4 h / Reflux 4.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0.25 h / 0 °C 4.2: 1 h / 20 °C 5.1: acetic acid / 1 h / 150 °C / Microwave irradiation 6.1: hydrogenchloride / water / 3 h / 100 °C
Multi-step reaction with 6 steps 1.1: ammonia / tetrahydrofuran / 16 h / 90 °C 2.1: triethylamine / dichloromethane / 0.17 h / 0 °C 2.2: 20 °C 3.1: ammonium chloride / water; ethanol / 0.33 h / 70 °C 3.2: 4 h / Reflux 4.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0.25 h / 0 °C 4.2: 1 h / 20 °C 5.1: 1 h / 150 °C / Microwave irradiation 6.1: hydrogenchloride / water / 3 h / 100 °C
  • 10
  • [ 131885-34-2 ]
  • {3-benzylamino-4-[(1,5-dimethyl-6-oxo-1,6-dihydro-pyridine-3-carbonyl)-amino]-phenyl}-carbamic acid tert-butyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: ammonia / tetrahydrofuran / 17 h / -70 - 90 °C 2.1: triethylamine / dichloromethane / 0.17 h / 0 °C 2.2: 20 °C 3.1: ammonium chloride / water; ethanol / 0.33 h / 70 °C 3.2: 4 h / Reflux 4.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0.25 h / 0 °C 4.2: 1 h / 20 °C
Multi-step reaction with 4 steps 1.1: ammonia / tetrahydrofuran / 16 h / 90 °C 2.1: triethylamine / dichloromethane / 0.17 h / 0 °C 2.2: 20 °C 3.1: ammonium chloride / water; ethanol / 0.33 h / 70 °C 3.2: 4 h / Reflux 4.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0.25 h / 0 °C 4.2: 1 h / 20 °C
  • 11
  • [ 131885-34-2 ]
  • (4-amino-3-benzylamino-phenyl)-carbamic acid tert-butyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: ammonia / tetrahydrofuran / 17 h / -70 - 90 °C 2.1: triethylamine / dichloromethane / 0.17 h / 0 °C 2.2: 20 °C 3.1: ammonium chloride / water; ethanol / 0.33 h / 70 °C 3.2: 4 h / Reflux
Multi-step reaction with 3 steps 1.1: ammonia / tetrahydrofuran / 16 h / 90 °C 2.1: triethylamine / dichloromethane / 0.17 h / 0 °C 2.2: 20 °C 3.1: ammonium chloride / water; ethanol / 0.33 h / 70 °C 3.2: 4 h / Reflux
  • 12
  • [ 131885-34-2 ]
  • N-[3-benzyl-2-(1,5-dimethyl-6-oxo-1,6-dihydro-pyridin-3-yl)-3H-benzoimidazol-5-yl]-acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: ammonia / tetrahydrofuran / 17 h / -70 - 90 °C 2.1: triethylamine / dichloromethane / 0.17 h / 0 °C 2.2: 20 °C 3.1: ammonium chloride / water; ethanol / 0.33 h / 70 °C 3.2: 4 h / Reflux 4.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0.25 h / 0 °C 4.2: 1 h / 20 °C 5.1: acetic acid / 1 h / 150 °C / Microwave irradiation
Multi-step reaction with 5 steps 1.1: ammonia / tetrahydrofuran / 16 h / 90 °C 2.1: triethylamine / dichloromethane / 0.17 h / 0 °C 2.2: 20 °C 3.1: ammonium chloride / water; ethanol / 0.33 h / 70 °C 3.2: 4 h / Reflux 4.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0.25 h / 0 °C 4.2: 1 h / 20 °C 5.1: 1 h / 150 °C / Microwave irradiation
  • 13
  • [ 109-01-3 ]
  • [ 131885-34-2 ]
  • N-benzyl-5-(4-methylpiperazin-1-yl)-2-nitroaniline [ No CAS ]
YieldReaction ConditionsOperation in experiment
93% In acetonitrile at 160℃; for 0.666667h; Microwave irradiation; N-benzyl-5-(4-methylpiperazin-1-yl)-2-nitroaniline E-1.1' N-benzyl-5-(4-methylpiperazin-1-yl)-2-nitroaniline E-1.1' Benzyl-(5-fluoro-2-nitro-phenyl)-amine E-1.1" (2.000 g; 6.579 mmol) is dissolved in acetonitril (10.000 ml). N-Methylpiperazine (1.460 ml; 13.158 mmol) is then added. The reaction mixture is stirred for 40 min at 160° C. in a Biotage XP Sixty microwave. The reaction mixture is poured into water and extracted with 3*50 ml DCM. The combined organic layer is dried over MgSO4 and concentrated under reduced pressure. The residue is used in the next step without further purification. Yield 93% (2.000 g; 6.128 mmol) HPLC-MS: (M+H)+=327; tRet=1.22 min; method LCMS BAS1
93% In acetonitrile at 160℃; for 0.666667h; 1 N-benzyl-5-(4-methylpiperazin- 1-yl)-2-nitroanhline E- 1.1' N-benzyl-5-(4-methylpiperazin- 1-yl)-2-nitroanhline E- 1.1’ Benzyl-(5-fluoro-2-nitro-phenyl)-amine E-1.1” (2.000 g; 6.579 mmol) is dissolved in acetonitril (10.000 ml). N-Methylpiperazine (1.460 ml; 13.158 mmol) is thenadded. The reaction mixture is stirred for 40 mm at 160°C in a Biotage XP Sixty microwave. The reaction mixture is poured into water and extracted with 3x50 ml DCM. The combined organic layer is dried over Mg504 and concentrated under reduced pressure. The residue is used in the next step without further purification. Yield 93% (2.000 g; 6.128 mmol)HPLC-MS: (M+H)+ = 327; tRet = 1.22 mm; method LCMS BAS1
33% With palladium diacetate; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1,4-dioxane at 100℃; for 12h; Inert atmosphere; 5-(4-Methylpiperazin-1-yl)-2-nitrophenol (6a) General procedure: Under the condition of nitrogen protection, intermediate compound 2a (5-iodo-2-nitrophenol, 26 mg, 0.1 mmol), 1-methylpiperazine (1, 10.0 mg, 0.1 mmol), Pd(OAc)2 (2.24 mg, 0.01 mmol), Xant-phos (29 mg, 0.05 mmol), and Cs2CO3,(97.5 mg, 0.3 mmol) were dissolved in 1,4-dioxane (6 mL) with a 25 mL duplex round bottom flask. Then, the reaction heated to 100 °C for12 h. The progress of the reaction was monitored by TLC, and the reaction solution concentrated by rotary evaporation after completion of the reaction. And then, product by column chromatography purification. Light yellow semi-solid (yield: 28%).
  • 14
  • [ 66698-28-0 ]
  • [ 131885-34-2 ]
  • N-benzyl-5-(4-(4-bromophenyl)piperazin-1-yl)-2-nitroaniline [ No CAS ]
YieldReaction ConditionsOperation in experiment
71% With potassium carbonate In dimethyl sulfoxide at 120℃; for 16h; Inert atmosphere; 98 N-benzyl-5-(4-(4-bromophenyl)piperazin-1-yl)-2-nitroaniline (LX) To a stirred solution of compound LW (4 g, 16.59 mmol) in DMSO (80 mL) under argon atmosphere were added potassium carbonate (4.58 g, 33.19 mmol) and G (4.08 g, 16.59 mmol) at RT. The reaction mixture was stiiied a t 20 °C for 16 h. The reaction mixture was diluted with ice cold water (100 mL) to obtain the solid. The solid was filtered, dissolved in CH2CI2 (50 mL), dried over anhydrous NSQ and concentrated under reduced pressure. The crude material was purified by silica gel column chromatography (eluent: 20% EiOAc Hexane) to afford compound LX (5.5 g, 11.80 mmol, 71%) as a brown solid. *H MR (400 MHz. DMSO-i): δ 8.82 (, /= 5.8 Hz, IH), 7.93 (d. J = 9.8 Hz, IH), 7.46-7.36 (m, 6H), 7.30-7.25 (m, IH), 6.90 (d, J= 9.2 Hz, 2H), 6.45 (dd, J= 9.8, 2,6 Hz, IH), 6.02 (d, J= 2.4 Hz., IH), 4.60 ( l J= 5.8 Hz, 2H), 3.53-3.47 (m, 4H), 3.24-3.17 (ni, 4H).
  • 15
  • [ 131885-34-2 ]
  • N1-benzyl-5-(4-(4-bromophenyl)piperazin-1-yl)benzene-1,2-diamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate / dimethyl sulfoxide / 16 h / 120 °C / Inert atmosphere 2: sodium tetrahydroborate; NiCl4*6H2O / methanol; dichloromethane / 2 h / 0 °C / Inert atmosphere
  • 16
  • [ 131885-34-2 ]
  • 1-benzyl-6-(4-(4-bromophenyl)piperazin-1-yl)-1H-benzo[d]imidazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: potassium carbonate / dimethyl sulfoxide / 16 h / 120 °C / Inert atmosphere 2: sodium tetrahydroborate; NiCl4*6H2O / methanol; dichloromethane / 2 h / 0 °C / Inert atmosphere 3: 12 h / 100 °C / Inert atmosphere
  • 17
  • [ 131885-34-2 ]
  • 1-benzyl-6-(4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)piperazin-1-yl)-1H-benzo[d]imidazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: potassium carbonate / dimethyl sulfoxide / 16 h / 120 °C / Inert atmosphere 2: sodium tetrahydroborate; NiCl4*6H2O / methanol; dichloromethane / 2 h / 0 °C / Inert atmosphere 3: 12 h / 100 °C / Inert atmosphere 4: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 8 h / 110 °C / Inert atmosphere
  • 18
  • [ 131885-34-2 ]
  • (R)-1-(5-(4-(4-(1-benzyl-1H-benzo[d]imidazol-6-yl)piperazine-1-yl)phenyl)pyridin-2-yl)-2-(2,4-difluorophenyl)-1,1-difluoro-3-(1H-tetrazol-1-yl)propan-2-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: potassium carbonate / dimethyl sulfoxide / 16 h / 120 °C / Inert atmosphere 2: sodium tetrahydroborate; NiCl4*6H2O / methanol; dichloromethane / 2 h / 0 °C / Inert atmosphere 3: 12 h / 100 °C / Inert atmosphere 4: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 8 h / 110 °C / Inert atmosphere 5: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / tetrahydrofuran; water / 8 h / 80 °C / Inert atmosphere
  • 19
  • [ 131885-34-2 ]
  • N-benzyl-5-(4-((4-chlorophenyl)sulfonyl)piperazin-1-yl)-2-nitroaniline [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: triethylamine / dimethyl sulfoxide / 16 h / 20 °C 2: triethylamine / dichloromethane / 16 h / 20 °C
  • 20
  • [ 110-85-0 ]
  • [ 131885-34-2 ]
  • benzyl-(2-nitro-5-piperazin-1-yl-phenyl)-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine In dimethyl sulfoxide at 20℃; for 16h;
  • 21
  • [ 131885-34-2 ]
  • 1-benzyl-6-fluoro-2-((7-fluoro-1H-indol-3-yl)methyl)-1H-benzo[d]imidazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: palladium on activated charcoal; hydrogen / methanol / 20 °C / 760.05 Torr / Inert atmosphere 2.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 5 h / 20 °C / Inert atmosphere 2.2: 1 h / 150 °C / Microwave irradiation; Inert atmosphere
  • 22
  • [ 131885-34-2 ]
  • [ 1250244-09-7 ]
YieldReaction ConditionsOperation in experiment
80% With palladium on activated charcoal; hydrogen In methanol at 20℃; Inert atmosphere; In a 100 mL flask with a magnetic stirring bar, N-benzyl-5-fluoro-2-nitroaniline (0.5 g, 2.03 mmol) and Pd/C (100 mg) weresuspended in 15 mL methanol. After sealing by rubber stopper, a2.0 L hydrogen balloon was connected with the reaction flask by asyringe needle. The reaction mixture was then stirred overnight atroom temperature. After removing the Pd/C by filtration, the solventwas removed by rotavapor. The residue was then purified bysilica gel column chromatography to afford 352 mg of N1-benzyl-5-fluorobenzene-1,2-diamine (80% yield).
With palladium on activated charcoal; hydrogen at 20℃; for 3h;
  • 23
  • [ 131885-34-2 ]
  • [ 1519538-34-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: hydrogen; palladium on activated charcoal / 3 h / 20 °C 2: tetrahydrofuran / 12 h / 20 °C
  • 24
  • [ 131885-34-2 ]
  • C14H10ClFN2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: hydrogen; palladium on activated charcoal / 3 h / 20 °C 2: tetrahydrofuran / 12 h / 20 °C 3: trichlorophosphate; phosphorus trichloride / 6 h / 90 °C
  • 25
  • [ 131885-34-2 ]
  • 1-benzyl-6-fluoro-2-(pyrrolidin-1-yl)-1H-benzo[d]imidazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: hydrogen; palladium on activated charcoal / 3 h / 20 °C 2: tetrahydrofuran / 12 h / 20 °C 3: trichlorophosphate; phosphorus trichloride / 6 h / 90 °C 4: 0.5 h / 200 °C / Microwave irradiation
Recommend Products
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 131885-34-2 ]

Fluorinated Building Blocks

Chemical Structure| 100460-79-5

[ 100460-79-5 ]

N-(4-Fluorobenzyl)-2-nitroaniline

Similarity: 0.98

Chemical Structure| 150812-21-8

[ 150812-21-8 ]

N1-(4-Fluorobenzyl)-3-nitrobenzene-1,4-diamine

Similarity: 0.94

Chemical Structure| 1263404-74-5

[ 1263404-74-5 ]

N1-(4-Fluorobenzyl)-4-nitrobenzene-1,3-diamine

Similarity: 0.94

Chemical Structure| 475278-46-7

[ 475278-46-7 ]

N-Ethyl-5-fluoro-2-nitroaniline

Similarity: 0.87

Chemical Structure| 774-22-1

[ 774-22-1 ]

N-Ethyl-4-fluoro-2-nitroaniline

Similarity: 0.87

Aryls

Chemical Structure| 100460-79-5

[ 100460-79-5 ]

N-(4-Fluorobenzyl)-2-nitroaniline

Similarity: 0.98

Chemical Structure| 150812-21-8

[ 150812-21-8 ]

N1-(4-Fluorobenzyl)-3-nitrobenzene-1,4-diamine

Similarity: 0.94

Chemical Structure| 1263404-74-5

[ 1263404-74-5 ]

N1-(4-Fluorobenzyl)-4-nitrobenzene-1,3-diamine

Similarity: 0.94

Chemical Structure| 475278-46-7

[ 475278-46-7 ]

N-Ethyl-5-fluoro-2-nitroaniline

Similarity: 0.87

Chemical Structure| 1221792-11-5

[ 1221792-11-5 ]

N-(4-Aminobenzyl)-2-nitroaniline

Similarity: 0.87

Amines

Chemical Structure| 100460-79-5

[ 100460-79-5 ]

N-(4-Fluorobenzyl)-2-nitroaniline

Similarity: 0.98

Chemical Structure| 150812-21-8

[ 150812-21-8 ]

N1-(4-Fluorobenzyl)-3-nitrobenzene-1,4-diamine

Similarity: 0.94

Chemical Structure| 1263404-74-5

[ 1263404-74-5 ]

N1-(4-Fluorobenzyl)-4-nitrobenzene-1,3-diamine

Similarity: 0.94

Chemical Structure| 475278-46-7

[ 475278-46-7 ]

N-Ethyl-5-fluoro-2-nitroaniline

Similarity: 0.87

Chemical Structure| 1221792-11-5

[ 1221792-11-5 ]

N-(4-Aminobenzyl)-2-nitroaniline

Similarity: 0.87

Nitroes

Chemical Structure| 100460-79-5

[ 100460-79-5 ]

N-(4-Fluorobenzyl)-2-nitroaniline

Similarity: 0.98

Chemical Structure| 150812-21-8

[ 150812-21-8 ]

N1-(4-Fluorobenzyl)-3-nitrobenzene-1,4-diamine

Similarity: 0.94

Chemical Structure| 1263404-74-5

[ 1263404-74-5 ]

N1-(4-Fluorobenzyl)-4-nitrobenzene-1,3-diamine

Similarity: 0.94

Chemical Structure| 475278-46-7

[ 475278-46-7 ]

N-Ethyl-5-fluoro-2-nitroaniline

Similarity: 0.87

Chemical Structure| 1221792-11-5

[ 1221792-11-5 ]

N-(4-Aminobenzyl)-2-nitroaniline

Similarity: 0.87