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Chemical Structure| 391912-54-2 Chemical Structure| 391912-54-2

Structure of 391912-54-2

Chemical Structure| 391912-54-2

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Product Details of [ 391912-54-2 ]

CAS No. :391912-54-2
Formula : C3H6ClNO2S
M.W : 155.60
SMILES Code : O=S(NC1CC1)(Cl)=O
English Name :Cyclopropylsulfamoyl Chloride
MDL No. :MFCD14529124
InChI Key :BFWHNTUPIABSEG-UHFFFAOYSA-N
Pubchem ID :22279368

Safety of [ 391912-54-2 ]

Application In Synthesis of [ 391912-54-2 ]

* 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 [ 391912-54-2 ]

[ 391912-54-2 ] Synthesis Path-Downstream   1~6

YieldReaction ConditionsOperation in experiment
The following sulfamoyl chlorides were prepared according to the above procedure from the corresponding amine: ... 4-Cyano-phenylsulfamoyl chloride, 4-Methoxy-phenylsulfamoyl chloride, Butylsulfamoyl chloride, Phenethylsulfamoyl chloride, Cyclopropylsulfamoyl chloride, 2,2,2-Trifluoroethylsulfamoyl chloride, 4-Fluoro-benzylsulfamoyl chloride, Furan-2-ylmethylsulfamoyl chloride, ...
With sulfuryl dichloride; triethylamine In dichloromethane Inert atmosphere; 6 Example 41-Step 1: Procedure for preparation of 41b General procedure: To a solution of sulfuryl chloride (2.28 g, 16.9 mmol, 1.0 eq) in dichloromethane (5mL) was added 41a (1 g, 16.9 mmol, 1.0 eq) and triethylamine (1.71 g, 16.9 mmol, 1.0 eq)under a nitrogen atmosphere at -10°C. The mixture was stirred for about 1 h. The reactionwas filtered and the filtrate was concentrated under nitrogen flow. The residue was trituratedwith tetrahydrofuran (10 mL) at 20 and then filtered. The filtrate was concentrated underreduced pressure to give crude 41b (propylsulfamoyl chloride) (1.2 g, 45% yield) as a colorlessoil, which was used directly in the next step.1H NMR: (400 MHZ CHLOROFORM-d) 0 ppm 3.02 (t, J = 7.2 Hz, 2 H), 1.54 - 1.66 (m, 2 H),0.96 (t, J = 7.2 Hz, 3 H).
  • 2
  • [ 391912-54-2 ]
  • [ 1136480-14-2 ]
  • [ 1187529-75-4 ]
YieldReaction ConditionsOperation in experiment
39% With pyridine at 20℃; 20 N-cyclopropyl-N'-{2-[(2-methoxybenzyl)amino]quinolin-6-yl}sulfamide Example 20 N-cyclopropyl-N'-{2-[(2-methoxybenzyl)amino]quinolin-6-yl}sulfamide N2-(2-Methoxy-benzyl)-quinoline-2,6diamine (example 10, step B, 40 mg, 0.143 mmol) was dissolved in 1 mL pyridine. Cyclopropylsulfamoyl chloride (29 mg, 0.186 mmol) was added and the reaction mixture was stirred at room temperature overnight. The solvent was evaporated off and the residue purified by flash chromatography on silica gel (heptane/ethyl acetate 90:10→34:66 gradient). The title compound was obtained as a yellow solid (22 mg, 39%), MS: m/e=397.5 (M+H+).
  • 3
  • [ 2088835-45-2 ]
  • [ 391912-54-2 ]
YieldReaction ConditionsOperation in experiment
24% With phosphorus pentachloride In toluene at 75℃; for 2h; 34.2 Step 2) cyclopropylsulfamoyl chloride Step 2) cyclopropylsulfamoyl chloride [0475] To a suspension of cyclopropanaminium cyclopropylsulfamate (3.33 g, 17.1 mmol) in anhydrous toluene (50.0 mL) was added phosphorus pentachloride (3.57 g, 17.1 mmol). The mixture was heated to 75 °C and stirred for 2 h and then cooled down to room temperature and filtered. The filtrate cake was washed with anhydrous toluene (10.0 mL). The filtrate was concentrated in vacuo to afford the title compound as brown liquid (0.65 g, yield 24%).
  • 4
  • [ 391912-54-2 ]
  • [ 2088835-20-3 ]
  • [ 2088835-53-2 ]
YieldReaction ConditionsOperation in experiment
44% With triethylamine In dichloromethane at 0 - 20℃; for 0.5h; 43.1 Step 1) N-cvclopropyl-5-((2,5-dichloropyrimidin-4-yl)amino)hexahydrocvclopentarc1pyrrole- 2(lH)-sulfonamide Step 1) N-cvclopropyl-5-((2,5-dichloropyrimidin-4-yl)amino)hexahydrocvclopentarc1pyrrole- 2(lH)-sulfonamide [0495] To a suspension of N-(2,5-dichloropyrimidin-4-yl)octahydrocyclopenta[c]pyrrol-5- amine (0.27 g, 0.987 mmol7) and TEA (0.70 mL, 5.00 mmol) in anhydrous DCM (10.0 mL) was slowly added a solution of cyclopropylsulfamoyl chloride (0.31 g, 1.98 mmol) in anhydrous DCM (5.0 mL) at 0 °C. After addition, the mixture was move to room temperature and stirred for another 30 min. The reaction was quenched by addition of water (20 mL) and allowed to stratification. The organic layer was separated and the aqueous layer was extracted with DCM (30 mL x 3). The combined organic layer was washed with brine (30 mL), dried over anhydrous Na2S04, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/PE (v/v) = 1/3) to afford the title compound as a yellow solid (0.17 g, yield 44%). MS (ESI, pos. ion) m/z: 392.1 [M+H]+; NMR (400 MHz, CDCb) δ (ppm): 8.02 (s, 1H), 5.70 (d, J = 7.7 Hz, 1H), 4.51-4.38 (m, 1H), 3.85 (s, 1H), 3.35-3.22 (m, 4H), 2.84-2.71 (m, 2H), 2.63-2.57 (m, 1H), 2.53-2.44 (m, 2H), 1.50- 1.37 (m, 2H), 0.75-0.70 (m, 4H).
44% With triethylamine In dichloromethane at 0 - 20℃; for 0.5h; 43.1 Step 1) N-Cyclopropyl-5 - ((2,5-dichloropyrimidin-4-yl) amino) hexahydrocyclopenta [c] pyrrole-Sulfonamide To a solution of N- (2,5-dichloropyrimidin-4-yl) octahydrocyclopenta [c] pyrrole-5-amine (0.27 g, 0.987 mmol) and Et3N (0.70 mL, 5.00 mmol) in anhydrous DCM (10.0 mL) was slowly added dropwise a solution of cyclopropylaminosulfonyl chloride (0.31 g, 1.98 mmol) in dry DCM (5.0 mL). After the dropwise addition, the reaction mixture was allowed to stand at room temperature for 30 minutes And then quenched with water (20 mL) and allowed to stand apart. The organic layer was separated and the aqueous layer was extracted with DCM (30 mL x 3). combined The organic phase was washed with saturated brine (30 mL), dried over anhydrous Na2SO4, filtered and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel (EtOAc / PE (v / v) = 1/3) to give the title compound as a yellow solid (0.17 g, yield 44%).
  • 5
  • [ 391912-54-2 ]
  • [ 1810076-23-3 ]
  • [ 2088835-05-4 ]
YieldReaction ConditionsOperation in experiment
22% With triethylamine In dichloromethane at 0 - 20℃; 34.3 Step 3) 5 -((5-chloro-2-((l -methyl- lH-pyrazol-4-yl)amino)pyrimidin-4-yl)amino)-N- cyclopropylhexahydrocyclopenta[clpyrrole-2(lH)-sulfonamide Step 3) 5 -((5-chloro-2-((l -methyl- lH-pyrazol-4-yl)amino)pyrimidin-4-yl)amino)-N- cyclopropylhexahydrocyclopenta[clpyrrole-2(lH)-sulfonamide [0476] To a suspension of 5-chloro-N2-(l -methyl- lH-pyrazol-4-yl)-N -(octahydrocyclopenta [c]pyrrol-5-yl)pyrimidine-2,4-diamine (0.10 g, 0.30 mmol) and TEA (0.21 mL, 1.50 mmol) in anhydrous DCM (10.0 mL) was added cyclopropylsulfamoyl chloride (0.10 g, 0.63 mmol) at 0 °C. The mixture was stirred at 0 °C for 15 min and then move to room temperature and stirred overnight. The resulting mixture was concentrated in vacuo. The residue was purified by silica gel column chromatography (DCM/(a solution of H3 in MeOH (3 M) (v/v) = 100/1 to 50/1) to get the title compound as a white solid (30 mg, yield 22%). MS (ESI, pos. ion) m/z: 453.2 [M+H]+; HRMS (ESI, pos. ion) m/z: 453.1585 [M+H]+, calculated value for Ci8H26ClN802S [M+H]+ is 453.1582; NMR (600 MHz, CDCb) δ (ppm): 7.86 (s, 1H), 7.64 (s, 1H), 7.49 (s, 1H), 6.62 (s, 1H), 5.33 (d, J = 7.3 Hz, 1H), 4.72 (d, J = 4.5 Hz, 1H), 4.38-4.27 (m, 1H), 3.88 (s, 3H), 3.32-3.25 (m, 4H), 2.78-2.72 (m, 2H), 2.62-2.57 (m, 1H), 2.51-2.45 (m, 2H), 1.48-1.41 (m, 2H), 0.73-0.65 (m, 4H); 13C NMR (150 MHz, CDCb) δ (ppm): 158.03, 157.65, 153.02, 131.05, 123.19, 121.01, 104.35, 54.24, 52.70, 40.51, 39.27, 24.82, 18.45, 6.90.
22% With triethylamine In dichloromethane at 0 - 20℃; for 0.25h; 34.3 Step 3)5 - ((5-chloro-2 - ((1-methyl-1H-pyrazol-Amino) pyrimidin-4-yl) amino) -N-cyclopropylhexahydrocyclopenta [c] pyrrole-2 (1H) -sulfonamide At 0 °CTo a solution of 5-chloro-N2- (1-methyl-1H-pyrazol-4-yl) -N4- (octahydrocyclopenta [c] pyrrol-Pyrimidine-2,4-diamine (0.10 g, 0.30 mmol) and Et3N (0.21 mL, 1.50 mmol) in dry DCM (10.0 mL) was added Cyclopropylaminosulfonyl chloride (0.10 g, 0.63 mmol). The reaction mixture was stirred at 0 & lt; 0 & gt; C for 15 minutes and then moved to room temperature Mix overnight After completion of the reaction, the reaction mixture was concentrated under reduced pressure, and the resulting residue was subjected to silica gel column chromatography (DCM / NH3 in MeOH solution(3M) (v / v) = 100/1 to 50/1) to give the title compound as a white solid (30 mg, yield 22%).
  • 6
  • [ 391912-54-2 ]
  • [ 2089610-75-1 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
With pyridine In tetrahydrofuran at 0 - 20℃; for 1h; Inert atmosphere; 5.I Step I : N-[(4R)-2-(dimethylsulfamovnisoxazolidin-4-yll-2-methyl-4-[5-(3,4,5-trichlorophenvn-5- Step I : N-[(4R)-2-(dimethylsulfamovnisoxazolidin-4-yll-2-methyl-4-[5-(3,4,5-trichlorophenvn-5- A solution of 2-chloro-4-[(5S)-5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-N-[(4R)- isoxazolidin-4-yl]benzamide (0.35 g) in tetrahydrofuran (5.5 mL) under nitrogen atmosphere, was treated with cyclopropylsulfamoyl chloride (0.161 g) (obtained in two steps by adding one equivalent of chlorosulfonic acid to three equivalents of cyclopropylamine in dichloromethane at 0°C, filtering and treating the solid residue with PCI5 in toluene at 75°C for 2 hours, the product being in solution can be recovered by decanting and evaporation of the solvent. ) followed by pyridine (0.065 g). After one hour stirring at 20°C, the reaction mixture was evaporated and the residue was submitted to chromatography over silica gel to yield the title compound that was characterized by NMR. HNMR (CDCI3, 400 MHz): 7.75-7.65 (m, 2H), 7.64 - 7.48 (m , 1 H), 7.50 (s, 2H), 7.42 (s, 1 H), 7.20 (d , 1 H), 5.45-5.35 (m , 1 H), 5.1 1 (s, 1 H), 4.48 (t, 1 H), 4.21 -4.15 (m , 1 H), 4.05 (d, 1 H), 3.94-3.86 (m , 1 H), 3.85-3.76 (m, 1 H), 3.68 (d , 1 H), 2.73-2-67 (m, 1 H), 0.90-0.65 (m, 4H).
 

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