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[ CAS No. 78682-33-4 ] {[proInfo.proName]}

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Chemical Structure| 78682-33-4
Chemical Structure| 78682-33-4
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Product Details of [ 78682-33-4 ]

CAS No. :78682-33-4 MDL No. :MFCD09904029
Formula : C10H8Cl2O Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W :215.08 Pubchem ID :-
Synonyms :

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Application In Synthesis of [ 78682-33-4 ]

* 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 [ 78682-33-4 ]

[ 78682-33-4 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 67198-26-9 ]
  • [ 78682-33-4 ]
  • 1-(4-Chloro-phenyl)-cyclopropanecarboxylic acid ((1R,2R)-2-dimethylamino-cyclohexyl)-methyl-amide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine In diethyl ether
  • 2
  • [ 72934-37-3 ]
  • [ 78682-33-4 ]
YieldReaction ConditionsOperation in experiment
With oxalyl dichloride;N,N-dimethyl-formamide; In dichloromethane; at 0 - 25℃; for 2h; Step 2.; 1-(4-chlorophenyl)cyclopropanecarbonyl chloride; A catalytic amount of N,N-dimethylformamide (DMF)(10 muL) was added to a mixture of 1-(4-chlorophenyl)cyclopropanecarboxylic acid (1.0 g, 5.1 mmol) and oxalyl chloride (2.2 mL, 25 mmol) in methylene chloride (5 mL) at 0° C. The resulting mixture was stirred at room temperature (about 25° C.) for 2 h. The volatiles were removed under reduced pressure, and the resulting residue was co-evaporated with toluene (2.x.) to provide the crude product, 1-(4-chlorophenyl)cyclopropanecarbonyl chloride, which was used in next step without further purification.
With oxalyl dichloride;N,N-dimethyl-formamide; In dichloromethane; at 0 - 20℃;Product distribution / selectivity; A suspension of commercially available 1-(4-chlorophenyl)cyclopropanecarboxylic acid (0.41 g, 2.1 mmol) in DCM (3 mL) was charged with oxalyl chloride (0.35 mL, 4.0 mmol) and N,N-dimethylformamide (5 muL) and stirred 2 h at ambient temperature. The reaction mixture was concentrated under reduced pressure. The resulting acid chloride was diluted with 1,2-dichloroethane (4 mL) and then added to a solution of methyl 6-(3-endo-amino-8-azabicyclo[3.2.1]octan-8-yl)nicotinate (0.18 g, 0.70 mmol), DIEA (0.24 mL, 1.4 mmol) and DMAP (10 mg) in 1,2-dichloroethane (2 mL). After stirring 2 h, the reaction mixture was diluted with EtOAc, washed with satd NaHCO3 and brine, dried (anhyd Na2SO4) and concentrated under reduced pressure. The residue was purified by chromatography (silica, EtOAc/Hex, 20:80 to 75:25) to afford the title compound (0.31 g, quant) as a white solid. 1H NMR (400 MHz, DCM-d2): delta 8.63 (s, 1H); MS (EI): 440 (MH+).; Example 56-[3-endo-({([1-(4-chlorophenyl)cyclopropyl]carbonyl}amino)-8-azabicyclo[3.2.1]oct-8-yl]pyridine-3-carboxamide A solution of commercially available 1-(4-chlorophenyl)-1-cyclopropanecarboxylic acid (7.4 g, 38 mmol) in DCM (75 mL) was chilled to 0° C. and treated with oxalyl chloride (6.6 mL, 76 mmol) and DMF (0.1 mL). The ice-water bath was removed and the reaction mixture was allowed to stir 3 hours at room temperature. The volatiles were removed under reduced pressure and co-evaporated with toluene (2.x.2 mL). The resulting acid chloride was diluted with DCE (40 mL) and added to a cooled (0° C.) solution of ethyl 3-endo-amino-8-azabicyclo[3.2.1]octane-8-carboxylate (5.0 g, 25 mmol) (made by adding ethyl carbonochloridate to the compound from Example 1 (B)), DIEA (8.8 mL, 50 mmol) and DMAP (154 mg, 1.3 mmol) in DCE (85 mL). The ice-water bath was removed and the reaction mixture was allowed to warm to room temperature. After 16 hours, the mixture was diluted with DCM (400 mL), washed with water (100 mL), then dried (anhyd Na2SO4) and filtered. The filtrate was concentrated under reduced pressure to give a residue that was purified by flash chromatography (silica gel, EtOAc/Hex, 50:50 to 80:20) to afford ethyl 3-endo-(1-(4-chlorophenyl)cyclopropane-carboxamido)-8-azabicyclo[3.2.1]octane-8-carboxylate (4.4 g, 42percent) as a yellow crystalline solid. 1H NMR (400 MHz, CDCl3): delta 7.41-7.34 (m, 4H), 5.73 (d, J=7.5 Hz, 1H), 4.23-4.02 (m, 5H), 2.21-1.96 (m, 2H), 1.90-1.81 (m, 2H), 1.62-1.57 (m, 2H), 1.56-1.44 (m, 2H), 1.25-1.09 (m, 5H), 1.05-1.00 (m, 2H).
With thionyl chloride;N,N-dimethyl-formamide; In toluene; at 20 - 50℃; 1-(4-Chlorophenyl)-cyclopropanecarboxylic acid (2 g, 10.2 mmol) was dissolved in 20 mL dry toluene. Thionyl chloride (2.42 g, 20.4 mmol) was added dropwise at room temperature and a catalytic amount of dry DMF was added. The resultant mixture was stirred at 50 0C for 2 hours. The reaction mixture was concentrated under high vacuum at 60 0C, the residue was dissolved in 10 ml_ DCM and thiosemicarbazide (1.12 g, 10.224 mmol) in a mixture of DMF: DCM (1 :4, 50 ml_) was added at 5-10 0C. The mixture was stirred at room temperature overnight under a nitrogen atmosphere and then the reaction mixture was concentrated under reduced pressure. The residue was dissolved in 200 ml. EtOAc and extracted with water (2x200mL), NaHCO3 (2x200 ml_) and brine (1x200 ml_). After concentration the product was precipitated by petroleum ether to give [[1-(4-chlorophenyl) cyclopropane-carbonyl]amino]thiourea in 32.7 percent yield (900 mg)MS: m/z 270 (M+H) HPLC purity: 99.0percent, NMR (300 MHz, DMSO-d6) delta ppm 1.01 (t, 2 H), 1.1.4 (m, 2H), 7.35 (d, 2 H) 7.45 (d, 2 H).
With oxalyl dichloride;N,N-dimethyl-formamide; In dichloromethane; for 2h; Example 392-[1-(4-chlorophenyl)cyclopropyl]-N-[1-oxo-4-(trifluoromethyl)phthalazin-2(1H)-yl]acetamideA solution of 1-(4-chlorophenyl)cyclopropanecarboxylic acid (0.3502 g, 1.781 mmol) and oxalyl dichloride (0.20 mL, 2.293 mmol) in dichloromethane (6 mL) containing a catalytic amount of DMF was stirred for 2 hours, concentrated, and re-dissolved in acetonitrile (5 mL) and THF (5 mL), and cooled to 0° C. A solution of (diazomethyl)trimethylsilane in Et2O (2M, 1.78 mL, 3.56 mmol) was added, stirred for 4 hours, allowing to warm to room temperature, concentrated, diluted with EtOAc, washed with saturated aqueous NaHCO3 and brine, dried (Na2SO4), filtered, and concentrated to give 355 mg of crude product as a dark oil, which was used without purification.A solution of the above crude 1-(1-(4-chlorophenyl)cyclopropyl)-2-diazoethanone (0.050 g, 0.23 mmol), the product from Example 11B (0.0505 g, 0.22 mmol), triethylamine (0.12 mL, 0.86 mmol), and silver benzoate (0.0504 g, 0.220 mmol) in DMF (1 mL) were stirred for 2 hours at 70° C., diluted with EtOAc, washed with saturated aqueous NaHCO3 and brine, dried (Na2SO4), and filtered. The residue was chromatographed on SiO2 (30percent EtOAc/hexanes) to give the title compound (23.0 mg, 0.055 mmol) as a white solid: 1H NMR (300 MHz, DMSO-d6) delta ppm 11.56 (s, 1H), 8.41-8.44 (m, 1H), 7.95-8.20 (m, 3H), 7.22-7.42 (m, 4H), 2.72 (d, J=1.0 Hz, 2H), 1.04-1.10 (m, 2H), 0.84-0.90 (m, 2H); MS (ESI+) M/Z 422 (M+H)+, 439 (M+NH4)+.
With thionyl chloride; In dichloromethane; at 50℃; for 1h;Inert atmosphere; General procedure: Thionyl chloride (4 eq) was added dropwise to an oven dried round bottomed flask containingcommercially available acid 1a-f (0.212 mmol ? 29.0 mmol) and dichloromethane (0.3 M). The reactionwas stirred at 50 °C for one hour. The resulting solution was concentrated under vacuum and redissolvedin dichloromethane (20 mL, 0.11 M) and added dropwise to a round bottom flask at 0 °C containing 4-piperidone (1.26 eq), triethylamine (7.5 eq), and THF (0.06 M). After 15 minutes the solution wasrefluxed at 50 °C for 24 hours. The reaction was carefully quenched with saturated aqueous ammoniumchloride and extracted with chloroform (3 x 20 mL). The resultant organic layers were combined anddried over Na2SO4, decanted and concentrated under vacuum. Product purification was achieved by silicagel flash chromatography (40percent ethyl acetate/60percent hexane).
With thionyl chloride;N,N-dimethyl-formamide; In dichloromethane; at 20℃; for 0.5h; CM. l-(4-chlorophenyl)-N-(5-methyl-6-(5-methyl-6-oxo-L6-dihvdropyridin-3- yl)pyridin-2-yl)cvclopropanecarboxamide; Step a: 1 -(4-chlorophenyl)-eta-(5-methyl-6-(5-methyl-6-oxo- 1 ,6-dhydropyridin-i- yl)pyridin-2-yl)cyclopropanecarboxamide; To a solution of l-(4-chlorophenyl)cyclopropanecarboxylic acid (39.3 mg, 0.2 mmol) in dichloromethane (2 mL) was added thionyl chloride (43.8 muL, 0.6 mmol) followed by DMF (1 drop) and the reaction was stirred at room temperature for 30 minutes and then the solvent was removed. Toluene (~ ImL) was added, mixed with the residue and then removed by evaporation. The residue was then dissolved in dichloromethane (1 mL) and a solution of 6'- methoxy-3,5'-dimethyl-2,3'-bipyridin-6-amine (46mg, 0.2 mmol) and triethyl amine (83.6 muL, 0.60 mmol) in dichloromethane (1 mL) was added. The reaction was stirred at room temperature for 12 hurs. The reaction was then concentrated. The residue was dissolved in DMSO and purified by reverse phase HPLC (10-99percent acetonitrile/water) to yield 62mg of the product. ESI-MS m/z calc. 407.1, found 408.2 (M+l)+. Retention time 2.07 minutes.

  • 3
  • [ 78682-33-4 ]
  • [ 56973-26-3 ]
  • [ 78682-34-5 ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In pyridine; diethyl ether; EXAMPLE 14 To a stirred suspension of 0.636 g. of 4-carbamoylimidazolium-5-olate in 15 ml of dry pyridine was dropwise added 1.61 g. of 1-(p-chlorophenyl)-1-cyclopropanecarbonyl chloride at a temperature below 5 C. in N2 atmosphere. After being stirred for two hours at 41-43 C., the reaction mixture was cooled to room temperature and 0.83 g. of triethylamine was added. Then the reaction mixture was concentrated under reduced pressure. To the residue was added diethyl ether and then separated crystals were filtered off, washed with diethyl ether, water and diisopropyl ether and dried to give 1.176 g. of 5-carbamoyl-1H-imidazole-4-yl 1'-(p-chlorophenyl)cyclopropane-1'-carboxylate, m.p. 190 C. (charred). Recrystallized was crude material from N,N-dimethylformamide and water. m.p.: 190-191 C.
  • 4
  • [ 69097-20-7 ]
  • [ 78682-33-4 ]
  • [ 1067187-87-4 ]
YieldReaction ConditionsOperation in experiment
Stage #1: tris(trimethylsilyloxy)ethylene; 1-(p-chlorophenyl)-1-cyclopropanecarbonyl chloride at 80 - 100℃; Inert atmosphere; Stage #2: With hydrogenchloride In 1,4-dioxane; water at 50 - 80℃;
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