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[ CAS No. 124276-34-2 ] {[proInfo.proName]}

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Chemical Structure| 124276-34-2
Chemical Structure| 124276-34-2
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Product Details of [ 124276-34-2 ]

CAS No. :124276-34-2 MDL No. :MFCD07374442
Formula : C10H9ClO2 Boiling Point : -
Linear Structure Formula :- InChI Key :QUIQAEWPDRXLFW-UHFFFAOYSA-N
M.W : 196.63 Pubchem ID :16769144
Synonyms :

Calculated chemistry of [ 124276-34-2 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.3
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 50.38
TPSA : 37.3 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) : -5.82 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.89
Log Po/w (XLOGP3) : 2.36
Log Po/w (WLOGP) : 2.39
Log Po/w (MLOGP) : 2.45
Log Po/w (SILICOS-IT) : 2.87
Consensus Log Po/w : 2.39

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -2.76
Solubility : 0.345 mg/ml ; 0.00176 mol/l
Class : Soluble
Log S (Ali) : -2.78
Solubility : 0.324 mg/ml ; 0.00165 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.21
Solubility : 0.121 mg/ml ; 0.000617 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.44

Safety of [ 124276-34-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P305+P351+P338 UN#:N/A
Hazard Statements:H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 124276-34-2 ]

* 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 [ 124276-34-2 ]

[ 124276-34-2 ] Synthesis Path-Downstream   1~45

  • 1
  • [ 124276-32-0 ]
  • [ 124276-34-2 ]
YieldReaction ConditionsOperation in experiment
77% Stage #1: 1-(3-chloro-phenyl)cyclopropanecarbonitrile With methanol; sodium hydroxide; water at 100℃; for 8h; Stage #2: With hydrogenchloride; water 257.3 Step 3: 1-(3-chlorophenyl)cyclopropanecarboxylic Acid; To a solution of 1-(3-chlorophenyl)cyclopropanecarbonitrile (2.1 g, 11.8 mmol) in methanol (10 ml), 35% NaOH (40 ml) was added and the mixture was heated to 100° C. for 8 hours. After cooling to room temperature, the resulting solution was evaporated under reduced pressure. And the aqueous layer was washed with ethyl ether, acidified with 2N HCl, and extracted organic layer with ethyl acetate. The organic solution was dried over magnesium sulfate, evaporated volatile solvent and dried under vacuum to obtain 1-(3-chlorophenyl)cyclopropanecarboxylic acid (1.8 g, 77% yield) as white solid.
62% With water; lithium hydroxide at 100℃; for 15h;
With lithium hydroxide In water at 100℃;
With lithium hydroxide In water; ethylene glycol at 100℃; for 24h;

YieldReaction ConditionsOperation in experiment
62%
  • 3
  • [ 124276-34-2 ]
  • [ 501698-47-1 ]
YieldReaction ConditionsOperation in experiment
With thionyl chloride In toluene at 115℃;
With thionyl chloride In dichloromethane at 22℃; for 15.5h; Inert atmosphere;
With thionyl chloride for 1h; Reflux; a 1 -(3-Chlorophenyl)cyclopropanecarboxylic acid (15 g, 76.3 mmol; CAS 124276-34-2) and thionyl chloride (90.8 g, 763 mmol) were heated to reflux until gas evaporation ceased (1 h). The mixture was cooled to RT and the excess thionyl chloride was evaporated under reduced pressure. The crude acid chloride was used without further purification.
With thionyl chloride; N,N-dimethyl-formamide at 20℃; for 5h; Intermediate 22A: 1-(3-Chlorophenyl)cyclopropanecarbonyl chloride 1-(3-Chlorophenyl)cyclopropanecarboxylic acid (2.0 g, 10.1 mmol) was stirred in thionyl chloride (12 mL) and DMF (2 drops) was added. The mixture was stirred at room temperature for 5 hours. NMR (sample prepared from MeOH) shows complete conversion to the methyl ester. The mixture was then concentrated at reduced pressure. The residue was diluted with heptane (3 mL) and re-concentrated twice to remove excess thionyl chloride to afford 1.94 g (87% yield) of the title compound as a yellow oil. Analysis of methyl ester: 1H NMR (250 MHz, DMSO-d6) δ[ppm] 7.45-7.22 (m, 4H), 3.55 (s, 3H), 1.56-1.40 (m, 2H), 1.30-1.15 (m, 2H).

  • 4
  • [ 124276-34-2 ]
  • [ 1252638-93-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: thionyl chloride / dichloromethane / 15.5 h / 22 °C / Inert atmosphere 2: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.83 h / 22 °C / Inert atmosphere
  • 5
  • [ 124276-34-2 ]
  • [ 1252638-10-0 ]
  • [ 1252641-14-7 ]
YieldReaction ConditionsOperation in experiment
41% Stage #1: 1-(3-chlorophenyl)cyclopropane-1-carboxylic acid With O-(1H-1,2,3-triazolo[4,5-b]pyridin-1-yl)-1,1,3,3-tetraethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 22℃; for 0.333333h; Inert atmosphere; Stage #2: (2S,4R)-4-(2-chlorophenylsulfonyl)-N-(1-cyanocyclopropyl)pyrrolidine-2-carboxamide In N,N-dimethyl-formamide at 22℃; for 18h; Inert atmosphere;
  • 6
  • [ 124276-34-2 ]
  • C14H21ClOSi [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 0 - 20 °C 2: tris(triphenylphosphine)ruthenium(II) chloride / benzene / 12 h / 50 °C / Inert atmosphere; Glovebox
  • 7
  • [ 124276-34-2 ]
  • C14H19ClOSi [ No CAS ]
  • C14H19ClOSi [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 0 - 20 °C 2: tris(triphenylphosphine)ruthenium(II) chloride / benzene / 12 h / 50 °C / Inert atmosphere; Glovebox 3: chloro(1,5-cyclooctadiene)rhodium(I) dimer; (S)-DTBM-SEGPHOS / tetrahydrofuran; cyclohexene / 24 h / 50 °C / Inert atmosphere; Glovebox
  • 8
  • [ 124276-34-2 ]
  • (1-(3-chlorophenyl)cyclopropyl)methanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
74% With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 2h;
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 2h; 143.1 (1-(3-chlorophenyl)cyclopropyl)methanol (2) To a stirred solution of 1-(3-chlorophenyl)cyclopropane-1 -carboxylic acid (1) (10 g, 51.02 mmol) in THF (200 mL) ware added LiAlhU drop wise at 0 °C and stirred atroom temperature for 2 h. The progress of the reaction was monitored by TLC and LCMS. Reaction mixture quenched with saturated NhUCI solution and extracted with ethyl acetate (2 x 100 mL). Combined organic layer and washed with water (2 X 50 mL), dried over sodium sulfate, concentrated under reduced pressure. The crude residue was purified by combi-flash compound eluted at 15% Ethyl acetate in pet ether to afford compound (1-(3-chlorophenyl)cyclopropyl)methanol (2). TLC system: 30% Ethyl acetate in hexane Rf: 0.6
  • 9
  • [ 6066-82-6 ]
  • [ 124276-34-2 ]
  • (2,5-dioxopyrrolidin-1-yl)-1-(3-chlorophenyl)cyclopropane-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
513 mg With pyridine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; for 2h; A] (2,5-Dioxopyrrolidin- i-yl) 1- (3-chlorophenyl)cyclopropane- 1 -carboxylate In a 100 mL flask, 1-(3-chlorophenyl)cyclopropanecarboxylic acid (0.50 g, 2.54 mmol, Eq: 1)was combined with DCM (15 ml) to give a colorless solution. At 0°C, pyridine (603 mg, 617 jil,7.63 mmol, Eq: 3), Ni -((ethylimino)methylene)-N3 ,N3-dimethylpropane- 1 ,3-diamine hydrochloride (634 mg, 3.31 mmol, Eq: 1.3), and i-hydroxypyrrolidine-2,5-dione (380 mg, 3.31 mmol, Eq: 1.3) were added, the ice-bath was removed, and the reaction allowed to proceed at RT for 2 hours. The reaction mixture was then quenched with sat. NH4C1 sol. and extracted withDCM (2 x, pH -4.5) .The organic layers were washed with sat. NaHCO3 (pH -8), combined, dried over Na2SO4, and concentrated in vacuo; after careful HV-drying, the crude material was crystallized from AcOEt/heptane to give 513 mg of the title compound as white solid.
  • 10
  • [ 124276-34-2 ]
  • (2S)-2-[[1-(3-chlorophenyl)cyclopropanecarbonyl]amino]-3-hydroxypropanoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: pyridine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 2 h / 0 - 20 °C 2: sodium hydrogencarbonate / tetrahydrofuran; 1,2-dimethoxyethane; water / 4 h / 20 °C
  • 11
  • [ 124276-34-2 ]
  • (2S)-3-[tert-butyl(dimethyl)silyl]oxy-2-[[1-(3-chlorophenyl)cyclopropanecarbonyl]amino]propanoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: pyridine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 2 h / 0 - 20 °C 2: sodium hydrogencarbonate / tetrahydrofuran; 1,2-dimethoxyethane; water / 4 h / 20 °C 3: 1H-imidazole / N,N-dimethyl-formamide / 20 °C
  • 12
  • [ 124276-34-2 ]
  • (2S)-2-[[1-(3-chlorophenyl)cyclopropanecarbonyl]amino]propanoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: pyridine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 2 h / 0 - 20 °C 2: sodium hydrogencarbonate / tetrahydrofuran; 1,2-dimethoxyethane; water / 4 h / 20 °C
  • 13
  • [ 124276-34-2 ]
  • 3’,4’-dimethoxy-2-(1H-tetrazol-5-yl)biphenyl-4-amine [ No CAS ]
  • 1-(3-chlorophenyl)-N-[3’,4’-dimethoxy-2-(1H-tetrazol-5-yl)biphenyl-4-yl]cyclopropanecarboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
48% With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; 1 Example 1 : 1 -(3-Chlorophenyl)-N-[3^4'-dimethoxy-2-(iH-tetrazol-5-yl)biphenyl-4-yl]cyclo- propanecarboxamide 3',4'-Dimethoxy-2-(iH-tetrazol-5-yl)biphenyl-4-amine (Intermediate 54A, 250 mg, 0.81 mmol) and 1 -(3-chlorophenyl)cyclopropane-1 -carboxylic acid (198 mg, 1.0 mmol) were dissolved in DMF (4 mL) and N,N-diisopropylethylamine (0.29 °L, 1 .7 mmol) and HATU (383 mg, 1.0 mmol) was added giving a yellow solution. This was stirred for overnight at RT. The mixture was diluted with EtOAc (50 mL) and washed with 2M aq. HCl (2 x 2 mL) and brine (2 mL), dried (Na2SC>4) , filtered and concentrated. The residue was purified via silica FCC (using a gradient of eluents; 99: 1 to 90: 10 DCM/MeOH) then via acidic preparative LC giving the title compound (191 mg, 48% yield) as a white solid.1H NMR (500 MHz, DMSO-d6) δ [ppm] 1.12 - 1.24 (m, 2H), 1.45 - 1.55 (m, 2H), 3.58 (s, 3H), 3.73 (s, 3H), 6.52 - 6.61 (m, 2H), 6.87 (d, J = 8.2 Hz, 1 H), 7.32 - 7.42 (m, 3H), 7.44 (d, J = 1.7 Hz, 1 H), 7.50 (d, J = 8.4 Hz, 1 H), 7.82 - 7.89 (m, 2H), 9.47 (s, 1 H).LCMS (Analytical Method F): Rt = 3.45 mins; MS (ESIpos) m/z = 476 (M+H)
  • 14
  • [ 124276-34-2 ]
  • N-[4-bromo-3-(1-[2-(trimethylsilyl)ethoxy]methyl}-1H-tetrazol-5-yl)phenyl]-1-(3-chlorophenyl)cyclopropanecarboxamide [ No CAS ]
  • N-[4-bromo-3-(2-[2-(trimethylsilyl)ethoxy]methyl}-2H-tetrazol-5-yl)phenyl]-1-(3-chlorophenyl)cyclopropanecarboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: thionyl chloride / 1 h / Reflux 2: pyridine / 3 h / 0 - 20 °C 3: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 1 h / 20 °C
  • 15
  • [ 124276-34-2 ]
  • 4N-[4-bromo-3-(1H-tetrazol-5-yl)phenyl]-1-(3-chlorophenyl)cyclopropanecarboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: thionyl chloride / 1 h / Reflux 2: pyridine / 3 h / 0 - 20 °C
  • 16
  • [ 124276-34-2 ]
  • 1-(3-chlorophenyl)-N-[4-(6-ethoxypyridin-3-yl)-3-(1H-tetrazol-5-yl)phenyl]cyclopropanecarboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: thionyl chloride / 1 h / Reflux 2: triethylamine / dichloromethane / 1 h / 0 °C
  • 17
  • [ 124276-34-2 ]
  • 1-(3-chlorophenyl)-N-{4-[6-(2-hydroxy-2-methylpropyl)pyridin-3-yl]-3-(1H-tetrazol-5-yl)phenyl}cyclopropanecarboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: thionyl chloride / 1 h / Reflux 2.1: pyridine / 3 h / 0 - 20 °C 3.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 1 h / 20 °C 3.2: 1 h / 100 °C 3.3: 5 h / 65 °C
  • 18
  • [ 124276-34-2 ]
  • C35H47ClN6O3Si2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: thionyl chloride / 1 h / Reflux 2.1: pyridine / 3 h / 0 - 20 °C 3.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 1 h / 20 °C 3.2: 1 h / 100 °C
  • 19
  • [ 124276-34-2 ]
  • methyl 5-amino-2-(1-cyclobutyl-1H-pyrazol-4-yl)benzoate [ No CAS ]
  • methyl 5-([1-(3-chlorophenyl)cyclopropyl]carbonyl}amino)-2-(1-cyclobutyl-1H-pyrazol-4-yl)benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 80℃; for 3h; Intermediate 155A: methyl 5-([1-(3-chlorophenyl)cyclopropyl]carbonyl}amino)-2-(1-cyclobutyl-1H-pyrazol-4-yl)benzoate methyl 5-amino-2-(1-cyclobutyl-1H-pyrazol-4-yl)benzoate (Intermediate 29A, 300 mg, 1 .11 mmol) and 1-(3-chlorophenyl)cyclopropane-1-carboxylic acid (260 mg, 1 .33 mmol) were dissolved in DMF (9 mL) and N,N-diisopropylethylamine (0.39 mL, 2.21 mmol) and HATU (505 mg, 1 .33 mmol) were added giving a light brown solution. This was stirred at 80 ° C for 3 h. The mixture was partitioned between EtOAc and water. The aqueous layer was extracted with EtOAc (3x 15 mL). The combined organic layers were washed with 2M aq. HCl (10 mL) and brine (10 mL), dried (Na2S04), filtered and concentrated. The residue was purified by Biotage Isolera chromatography to give title compound (372 mg, 75% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ [ppm] 1 .1 5 - 1 .18 (m, 2H), 1 .46 - 1 .49 (m, 2H), 1 .75 -1 .81 (m, 2H), 2.34 -2.42 (m, 2H), 2.43 -2 48 (m, 2H), 3.74 (s, 3H), 4.83 (quint, 1 H), 7.34 - 7.43 (m, 5H), 7.49 (d, 1 H), 7.72 (dd, 1 H), 7.85 (d, 1 H), 7.92 (d, 1 H), 9.39 (s, 1 H). LCMS (method 1 ): Rt = 1 .37 min; MS (ESIPos) m/z = 450 (M+H)
  • 20
  • [ 124276-34-2 ]
  • cyclopentyl 4-([1-(3-chlorophenyl)cyclopropyl]carbonyl}amino)-2-(1H-tetrazol-5-yl)benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N,N-dimethyl-formamide; thionyl chloride / 5 h / 20 °C 2: pyridine / dichloromethane / 0.5 h
  • 21
  • [ 124276-34-2 ]
  • sec-butyl 4-([1-(3-chlorophenyl)cyclopropyl]carbonyl}amino)-2-(1H-tetrazol-5-yl)benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N,N-dimethyl-formamide; thionyl chloride / 5 h / 20 °C 2: pyridine / dichloromethane / 0.5 h / 20 °C
  • 22
  • [ 67-56-1 ]
  • [ 124276-34-2 ]
  • methyl 1-(3-chlorophenyl)cyclopropanecarboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 1-(3-chlorophenyl)cyclopropane-1-carboxylic acid With thionyl chloride; N,N-dimethyl-formamide at 20℃; for 5h; Stage #2: methanol 1-(3-Chlorophenyl)cyclopropanecarboxylic acid (2.0 g, 10.1 mmol) was stirred in thionyl chloride (12 mL) and DMF (2 drops) was added. The mixture was stirred at room temperature for 5 hours. NMR (sample prepared from MeOH) shows complete conversion to the methyl ester. The mixture was then concentrated at reduced pressure. The residue was diluted with heptane (3 mL) and re-concentrated twice to remove excess thionyl chloride to afford 1.94 g (87% yield) of the title compound as a yellow oil. Analysis of methyl ester: 1H NMR (250 MHz, DMSO-d6) δ[ppm] 7.45-7.22 (m, 4H), 3.55 (s, 3H), 1.56-1.40 (m, 2H), 1.30-1.15 (m, 2H).
  • 23
  • [ 124276-34-2 ]
  • ethyl 4-amino-2-(1H-tetrazol-5-yl)benzoate [ No CAS ]
  • ethyl 4-([1-(3-chlorophenyl)cyclopropyl]carbonyl}amino)-2-(1H-tetrazol-5-yl)benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
9% With dmap; N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 20℃; for 72h; 1 Example 1 Ethyl 4-amino-2-(1H-tetrazol-5-yl)benzoate (Int. 5A, 360 mg, 1.54 mmol) and 1-(3-chlorophenyl)cyclopropane-1-carboxylic acid (364 mg, 1.85 mmol) were dissolved in DMF (3 mL) and N,N-diisopropylethylamine (0.81 mL, 4.6 mmol), 4-dimethylaminopyridine (68 mg, 0.56 mmol) and HATU (705 mg, 1.85 mmol) were added. This was stirred for 3 days at RT. The mixture was concentrated at reduced pressure to remove excess DMF then diluted with EtOAc (50 mL) and washed with 1M aq. HCl (20 mL), brine (2*20 mL), dried (Na2SO4), filtered and concentrated at reduced pressure. The residue was purified by Biotage isolera chromatography (silica gel, eluting with DCM-MeOH, 49:1 to 4:1), then re-purified by preparative HPLC (Method B) to afford 60 mg (9% yield) of the title compound as a yellow solid. 1H NMR (500 MHz, DMSO-d6) δ[ppm] 9.69 (s, 1H), 8.02-7.85 (m, 3H), 7.46-7.30 (m, 4H), 4.09 (q, J=7.1 Hz, 2H), 1.53-1.47 (m, 2H), 1.25-1.17 (m, 2H), 1.05 (t, J=7.1 Hz, 3H). LCMS (Analytical Method F): Rt=3.29 mins; MS (ESIpos) m/z=412 (M+H)+.
  • 24
  • [ 124276-34-2 ]
  • C20H29BClNO3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 12 h / 20 °C 2: bis(1,5-cyclooctadiene)diiridium(I) dichloride; C49H56BN3Si / tetrahydrofuran / 36 h / 60 °C / Schlenk technique
  • 25
  • [ 124276-34-2 ]
  • [ 109-89-7 ]
  • C14H18ClNO [ No CAS ]
YieldReaction ConditionsOperation in experiment
1.23 g With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 12h;
  • 26
  • [ 1529-41-5 ]
  • [ 124276-34-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide / water / 12 h / 50 °C 2: lithium hydroxide / water; ethylene glycol / 24 h / 100 °C
  • 27
  • [ 524-38-9 ]
  • [ 124276-34-2 ]
  • 1,3-dioxoisoindolin-2-yl 1-(3-chlorophenyl)cyclopropane-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃;
  • 28
  • [ 124276-34-2 ]
  • (4-chlorophenyl)(1-(3-chlorophenyl)cyclopropyl)methanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 0 - 20 °C 2: Dess-Martin periodane / ethyl acetate / 3 h / 0 - 20 °C 3: tetrahydrofuran / 3 h / -30 °C / Heating
  • 29
  • [ 124276-34-2 ]
  • methyl (((4-chlorophenyl)(1-(3-chlorophenyl)cyclopropyl)methyl)carbonyl)-L-leucinate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 0 - 20 °C 2.1: Dess-Martin periodane / ethyl acetate / 3 h / 0 - 20 °C 3.1: tetrahydrofuran / 3 h / -30 °C / Heating 4.1: triethylamine; di(succinimido) carbonate / acetonitrile / 4 h / 0 - 20 °C 4.2: 20 °C
  • 30
  • [ 124276-34-2 ]
  • [ 1213775-28-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 0 - 20 °C 2: Dess-Martin periodane / ethyl acetate / 3 h / 0 - 20 °C
  • 31
  • [ 124276-34-2 ]
  • (3-chlorophenyl)(1-(3-chlorophenyl)cyclopropyl)methanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 0 - 20 °C 2: Dess-Martin periodane / ethyl acetate / 3 h / 0 - 20 °C 3: tetrahydrofuran / 3 h / -30 °C / Heating
  • 32
  • [ 124276-34-2 ]
  • methyl (((3-chlorophenyl)(1-(3-chlorophenyl)cyclopropyl)methoxy)carbonyl)-L-leucinate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 0 - 20 °C 2.1: Dess-Martin periodane / ethyl acetate / 3 h / 0 - 20 °C 3.1: tetrahydrofuran / 3 h / -30 °C / Heating 4.1: triethylamine; di(succinimido) carbonate / acetonitrile / 0 - 20 °C 4.2: 16 h / 20 °C
  • 33
  • [ 124276-34-2 ]
  • (((3-chlorophenyl)(1-(3-chlorophenyl)cyclopropyl)methoxy)carbonyl)-L-leucine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 0 - 20 °C 2.1: Dess-Martin periodane / ethyl acetate / 3 h / 0 - 20 °C 3.1: tetrahydrofuran / 3 h / -30 °C / Heating 4.1: triethylamine; di(succinimido) carbonate / acetonitrile / 0 - 20 °C 4.2: 16 h / 20 °C 5.1: lithium hydroxide; water / tetrahydrofuran / 3 h / 0 - 20 °C
  • 34
  • [ 124276-34-2 ]
  • methyl (2S)-2-((2S)-2-((((3-chlorophenyl)(1-(3-chlorophenyl)cyclopropyl)methoxy)carbonyl)amino)-4-methylpentanamido)-3-((S)-2-oxopyrrolidin-3-yl)propanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 0 - 20 °C 2.1: Dess-Martin periodane / ethyl acetate / 3 h / 0 - 20 °C 3.1: tetrahydrofuran / 3 h / -30 °C / Heating 4.1: triethylamine; di(succinimido) carbonate / acetonitrile / 0 - 20 °C 4.2: 16 h / 20 °C 5.1: lithium hydroxide; water / tetrahydrofuran / 3 h / 0 - 20 °C 6.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 16 h / 0 - 20 °C
  • 35
  • [ 124276-34-2 ]
  • (3-chlorophenyl)(1-(3-chlorophenyl)cyclopropyl)methyl ((S)-1-(((S)-1-hydroxy-3-((S)-2-oxopyrrolidin-3-yl)propan-2-yl)amino)-4-methyl-1-oxopentan-2-yl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 0 - 20 °C 2.1: Dess-Martin periodane / ethyl acetate / 3 h / 0 - 20 °C 3.1: tetrahydrofuran / 3 h / -30 °C / Heating 4.1: triethylamine; di(succinimido) carbonate / acetonitrile / 0 - 20 °C 4.2: 16 h / 20 °C 5.1: lithium hydroxide; water / tetrahydrofuran / 3 h / 0 - 20 °C 6.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 16 h / 0 - 20 °C 7.1: lithium borohydride / tetrahydrofuran / 2 h / 0 °C
  • 36
  • [ 124276-34-2 ]
  • (3-chlorophenyl)(1-(3-chlorophenyl)cyclopropyl)methyl ((S)-4-methyl-1-oxo-1-(((S)-1-oxo-3-((S)-2-oxopyrrolidin-3-yl)propan-2-yl)amino)pentan-2-yl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 0 - 20 °C 2.1: Dess-Martin periodane / ethyl acetate / 3 h / 0 - 20 °C 3.1: tetrahydrofuran / 3 h / -30 °C / Heating 4.1: triethylamine; di(succinimido) carbonate / acetonitrile / 0 - 20 °C 4.2: 16 h / 20 °C 5.1: lithium hydroxide; water / tetrahydrofuran / 3 h / 0 - 20 °C 6.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 16 h / 0 - 20 °C 7.1: lithium borohydride / tetrahydrofuran / 2 h / 0 °C 8.1: Dess-Martin periodane / 3 h / 0 - 20 °C
  • 37
  • [ 124276-34-2 ]
  • (3-chlorophenyl)(1-(3-chlorophenyl)cyclopropyl)methyl ((2S)-1-(((2S)-4-(cyclopropylamino)-3-hydroxy-4-oxo-1-((S)-2-oxopyrrolidin-3-yl)butan-2-yl)amino)-4-methyl-1-oxopentan-2-yl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 9 steps 1.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 0 - 20 °C 2.1: Dess-Martin periodane / ethyl acetate / 3 h / 0 - 20 °C 3.1: tetrahydrofuran / 3 h / -30 °C / Heating 4.1: triethylamine; di(succinimido) carbonate / acetonitrile / 0 - 20 °C 4.2: 16 h / 20 °C 5.1: lithium hydroxide; water / tetrahydrofuran / 3 h / 0 - 20 °C 6.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 16 h / 0 - 20 °C 7.1: lithium borohydride / tetrahydrofuran / 2 h / 0 °C 8.1: Dess-Martin periodane / 3 h / 0 - 20 °C 9.1: pyridine / dichloromethane / 0.5 h / 0 °C 9.2: 16 h / 0 - 20 °C
  • 38
  • [ 124276-34-2 ]
  • (3-chlorophenyl)(1-(3-chlorophenyl)cyclopropyl)methyl ((S)-1-(((S)-4-(cyclopropylamino)-3,4-dioxo-1-((S)-2-oxopyrrolidin-3-yl)butan-2-yl)amino)-4-methyl-1-oxopentan-2-yl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 10 steps 1.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 0 - 20 °C 2.1: Dess-Martin periodane / ethyl acetate / 3 h / 0 - 20 °C 3.1: tetrahydrofuran / 3 h / -30 °C / Heating 4.1: triethylamine; di(succinimido) carbonate / acetonitrile / 0 - 20 °C 4.2: 16 h / 20 °C 5.1: lithium hydroxide; water / tetrahydrofuran / 3 h / 0 - 20 °C 6.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 16 h / 0 - 20 °C 7.1: lithium borohydride / tetrahydrofuran / 2 h / 0 °C 8.1: Dess-Martin periodane / 3 h / 0 - 20 °C 9.1: pyridine / dichloromethane / 0.5 h / 0 °C 9.2: 16 h / 0 - 20 °C 10.1: Dess-Martin periodane / ethyl acetate / 3 h / 0 - 20 °C
  • 39
  • [ 124276-34-2 ]
  • methyl (2S)-2-((((3-chlorophenyl)(1-(3-chlorophenyl)cyclopropyl)methoxy)carbonyl)amino)-3-cyclohexylpropanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 0 - 20 °C 2.1: Dess-Martin periodane / ethyl acetate / 3 h / 0 - 20 °C 3.1: tetrahydrofuran / 3 h / -30 °C / Heating 4.1: triethylamine; di(succinimido) carbonate / acetonitrile / 4 h / 0 - 20 °C 4.2: 16 h / 20 °C
  • 40
  • [ 124276-34-2 ]
  • (2S)-2-((((3-chlorophenyl)(1-(3-chlorophenyl)cyclopropyl)methoxy)carbonyl)amino)-3-cyclohexylpropanoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 0 - 20 °C 2.1: Dess-Martin periodane / ethyl acetate / 3 h / 0 - 20 °C 3.1: tetrahydrofuran / 3 h / -30 °C / Heating 4.1: triethylamine; di(succinimido) carbonate / acetonitrile / 4 h / 0 - 20 °C 4.2: 16 h / 20 °C 5.1: lithium hydroxide; water / tetrahydrofuran / 3 h / 0 - 20 °C
  • 41
  • [ 124276-34-2 ]
  • methyl (2S)-2-((2S)-2-((((3-chlorophenyl)(1-(3-chlorophenyl)cyclopropyl)methoxy)carbonyl)amino)-3-cyclohexylpropanamido)-3-((S)-2-oxopyrrolidin-3-yl)propanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 0 - 20 °C 2.1: Dess-Martin periodane / ethyl acetate / 3 h / 0 - 20 °C 3.1: tetrahydrofuran / 3 h / -30 °C / Heating 4.1: triethylamine; di(succinimido) carbonate / acetonitrile / 4 h / 0 - 20 °C 4.2: 16 h / 20 °C 5.1: lithium hydroxide; water / tetrahydrofuran / 3 h / 0 - 20 °C 6.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 16 h / 0 - 20 °C
  • 42
  • [ 124276-34-2 ]
  • (3-chlorophenyl)(1-(3-chlorophenyl)cyclopropyl)methyl ((S)-3-cyclohexyl-1-(((S)-1-hydroxy-3-((S)-2-oxopyrrolidin-3-yl)propan-2-yl)amino)-1-oxopropan-2-yl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 0 - 20 °C 2.1: Dess-Martin periodane / ethyl acetate / 3 h / 0 - 20 °C 3.1: tetrahydrofuran / 3 h / -30 °C / Heating 4.1: triethylamine; di(succinimido) carbonate / acetonitrile / 4 h / 0 - 20 °C 4.2: 16 h / 20 °C 5.1: lithium hydroxide; water / tetrahydrofuran / 3 h / 0 - 20 °C 6.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 16 h / 0 - 20 °C 7.1: lithium borohydride / tetrahydrofuran / 2 h / 0 °C
  • 43
  • [ 124276-34-2 ]
  • (3-chlorophenyl)(1-(3-chlorophenyl)cyclopropyl)methyl ((S)-3-cyclohexyl-1-oxo-1-(((S)-1-oxo-3-((S)-2-oxopyrrolidin-3-yl)propan-2-yl)amino)propan-2-yl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 0 - 20 °C 2.1: Dess-Martin periodane / ethyl acetate / 3 h / 0 - 20 °C 3.1: tetrahydrofuran / 3 h / -30 °C / Heating 4.1: triethylamine; di(succinimido) carbonate / acetonitrile / 4 h / 0 - 20 °C 4.2: 16 h / 20 °C 5.1: lithium hydroxide; water / tetrahydrofuran / 3 h / 0 - 20 °C 6.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 16 h / 0 - 20 °C 7.1: lithium borohydride / tetrahydrofuran / 2 h / 0 °C 8.1: Dess-Martin periodane / ethyl acetate / 3 h / 0 - 20 °C
  • 44
  • [ 124276-34-2 ]
  • (3-chlorophenyl)(1-(3-chlorophenyl)cyclopropyl)methyl ((2S)-3-cyclohexyl-1-(((2S)-4-(cyclopropylamino)-3-hydroxy-4-oxo-1-((S)-2-oxopyrrolidin-3-yl)butan-2-yl)amino)-1-oxopropan-2-yl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 9 steps 1.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 0 - 20 °C 2.1: Dess-Martin periodane / ethyl acetate / 3 h / 0 - 20 °C 3.1: tetrahydrofuran / 3 h / -30 °C / Heating 4.1: triethylamine; di(succinimido) carbonate / acetonitrile / 4 h / 0 - 20 °C 4.2: 16 h / 20 °C 5.1: lithium hydroxide; water / tetrahydrofuran / 3 h / 0 - 20 °C 6.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 16 h / 0 - 20 °C 7.1: lithium borohydride / tetrahydrofuran / 2 h / 0 °C 8.1: Dess-Martin periodane / ethyl acetate / 3 h / 0 - 20 °C 9.1: pyridine / dichloromethane / 0.5 h / 0 °C 9.2: 16 h / 0 - 20 °C
  • 45
  • [ 124276-34-2 ]
  • (3-chlorophenyl)(1-(3-chlorophenyl)cyclopropyl)methyl ((S)-3-cyclohexyl-1-(((S)-4-(cyclopropylamino)-3,4-dioxo-1-((S)-2-oxopyrrolidin-3-yl)butan-2-yl)amino)-1-oxopropan-2-yl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 10 steps 1.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 0 - 20 °C 2.1: Dess-Martin periodane / ethyl acetate / 3 h / 0 - 20 °C 3.1: tetrahydrofuran / 3 h / -30 °C / Heating 4.1: triethylamine; di(succinimido) carbonate / acetonitrile / 4 h / 0 - 20 °C 4.2: 16 h / 20 °C 5.1: lithium hydroxide; water / tetrahydrofuran / 3 h / 0 - 20 °C 6.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 16 h / 0 - 20 °C 7.1: lithium borohydride / tetrahydrofuran / 2 h / 0 °C 8.1: Dess-Martin periodane / ethyl acetate / 3 h / 0 - 20 °C 9.1: pyridine / dichloromethane / 0.5 h / 0 °C 9.2: 16 h / 0 - 20 °C 10.1: Dess-Martin periodane / ethyl acetate / 0 - 20 °C
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