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[ CAS No. 41720-98-3 ]

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2D
Chemical Structure| 41720-98-3
Chemical Structure| 41720-98-3
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Product Details of [ 41720-98-3 ]

CAS No. :41720-98-3MDL No. :MFCD07783026
Formula : C5H11N Boiling Point : 100.2°C at 760 mmHg
Linear Structure Formula :-InChI Key :-
M.W :85.15Pubchem ID :641544
Synonyms :

Computed Properties of [ 41720-98-3 ]

TPSA : 12 H-Bond Acceptor Count : 1
XLogP3 : 0.7 H-Bond Donor Count : 1
SP3 : 1.00 Rotatable Bond Count : 0

Safety of [ 41720-98-3 ]

Signal Word:DangerClass:3,8
Precautionary Statements:P242-P264-P271-P280-P301+P330+P331-P304+P340-P305+P351+P338-P310-P363-P370+P378-P403+P233-P501UN#:2733
Hazard Statements:H225-H314Packing Group:
GHS Pictogram:

Application In Synthesis of [ 41720-98-3 ]

  • Downstream synthetic route of [ 41720-98-3 ]

[ 41720-98-3 ] Synthesis Path-Downstream   1~8

  • 1
  • [ 23418-85-1 ]
  • [ 41720-98-3 ]
  • [ 460747-73-3 ]
  • 2
  • [ 157007-54-0 ]
  • [ 41720-98-3 ]
YieldReaction ConditionsOperation in experiment
98% With hydrogenchloride; In 1,4-dioxane; for 0.5h; Step B: (i)-2-Methylpyrrolidine Hydrochloride; (i?)-ter/-Butyl 2-methylpyrrolidine-l-carboxylate (22.7 g, 123 mmol) was dissolved in a 4 M hydrogen chloride solution in dioxane (100 mL) and the reaction was stirred for 30 min. TLC (2:1, ethyl acetate/hexanes) confirmed that there was no starting material left. The solvent was removed under reduced pressure. The crude residue was dissolved in acetonitrile and toluene. The solvent was removed under reduced pressure and the resulting white powder was dried overnight under reduced pressure to give the title compound (14.6 g) in 98percent yield. 1H NMR (400 MHz, CDCl3) delta 1.55 (d, J= 6.57 Hz, 3 H), 1.66 - 1.77 (m, 1 H), 1.95 - 2.04 (m, 1 H), 2.05 - 2.23 (m, 2 H), 3.25 - 3.36 (m, 1 H), 3.37 - 3.48 (m, 1 H), 3.62 - 3.74 (m, 1 H), 9.38 (s, 1 H), 9.86 (s, 1 H).
95.6% With hydrogenchloride; In ethyl acetate; at 20℃; for 2.08333h;pH 1.0; Example 4 Preparation of 2-(R)-methyl-pyrrolidine.HCl (6) 2-(R)-Methyl-pyrrolidine-1-carboxylic tert-butyl ester (compound (5), 12 g, 64 mmol), obtained from Example 1, Step 4, was dissolved in ethyl acetate and HCl gas was passed through it for 5 minutes until the pH of the reaction mixture was below 1. The reaction mixture was mixed at room temperature for 2 hours. HPLC showed the absence of the starting material. The reaction mixture was concentrated to leave a residue, which was triturated with methyl tert-butyl ether (3*30 mL) while decanting the liquors.
With hydrogenchloride; acetic acid; at 20℃; for 1h; To a 500 mL flask is placed 2R-Methyl-pyrrolidine-l-carboxylic acid tert-butyl ester (see Intermediate 6) (5.4 g, 29.1 mmol) and HC1 / acetic acid (1M, 45 mL) at ambient temperature. The mixture is stirred for 1 hour and then concentrated to an oily solid. The solid is triturated with 2:1 diethyl ether / hexane and dried to give 3.02 g of pure titled compound. 400 MHz NMR (Methanol- d4) 8 3.67 (m, 1H), 3.35 (m, 2H), 2.25 (m, 1H) 2.1 (m, 2H), 1.66 (m, 1H), and 1.43 (d, 7= 8Hz, 3H)
  • 3
  • [ 41720-98-3 ]
  • [ 590-17-0 ]
  • [ 904679-05-6 ]
YieldReaction ConditionsOperation in experiment
100% With triethylamine; In methanol; at 0 - 20℃; for 1h; (Step 1) <strong>[41720-98-3](R)-2-methylpyrrolidine hydrochloride</strong> (1.66 g, 13.7 mmol) prepared in a similar manner to the method described in was dissolved in methanol (20 mL) and the solution was added with triethylamine (9.55 mL, 68.5 mmol) and bromoacetonitrile (2.86 mL, 41.1 mmol) under ice bath, followed by stirring at room temperature for 1 hour. The solvent was evaporated under reduced pressure and the residue was added with saturated brine and extracted with chloroform. After washing with saturated brine, the organic layer was dried over anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate (7:3)) to obtain (R)-1-cyanomethyl-2-methylpyrrolidine (1.70 g, 100 percent) as a clear oily substance. 1H NMR (CDCl3, deltappm): 1.10 (d, J = 6.0 Hz, 3H), 1.39-1.53 (m, 1H), 1.71-1.91 (m, 2H), 1.94-2.08 (m, 1H), 2.53-2.66 (m, 2H), 3.03 (td, J =3.2 Hz, 8.4 Hz, 1H), 3.68 (s, 2H).
  • 4
  • [ 1005402-21-0 ]
  • [ 41720-98-3 ]
  • CEP-19938 [ No CAS ]
YieldReaction ConditionsOperation in experiment
48% 6-[4-(3-Chloropropoxy)phenyl]-2-methyl-2H-pyridazin-3-one (1.5 g, 5.4 mmol), K2CO3 (2.2 g 16.2 mmol), NaI (805 mg, 5.4 mmol) R-methylpyrrolidine HCl (1.3 g, 10.8 mmol) in CH3CN (30 mL) was heated under N2 at 90° C. for 2 days. The reaction was filtered and concentrated. The residue was dissolved in EtOAc and washed with 2N Na2CO3 (1.x.), NaCl solution (1.x.) dried (MgSO4) and concentrated. The product was purified by ISCO chromatography (80 g silica gel column, 95:5 DCM:MeOH). The fractions were combined and concentrated to yield 850 mg (48percent) of free base. The HCl was prepared by adding a 1N HCl-ether solution to the based in ether. The product was collected, and recrystallized from CH3CN-ether. mp 183-185° C. 1H NMR (DMSO-d6) delta 1.38 (d, 3H), 1.62 (m, 1H), 1.92-1.3.1 (m, 3H), 3.4 (m, 3H), 3.7 (m, 1H), 3.7 (s, 3H), 4.15 (m, 2H), 7.0-7.17 (m, 3H), 7.8 (d, 2H), 8.0 (d, 1H), 10.1 (s, 1H). MS m/z=328 (M+H).
  • 5
  • [ 1005402-22-1 ]
  • [ 41720-98-3 ]
  • Irdabisant [ No CAS ]
YieldReaction ConditionsOperation in experiment
A mixture of the product from step 2 (5.5 g, 21 mmol), K2CO3 (3.5 eq, 10.1 g), 100 mg of NaI, and R-2-methylpyrrolidine hydrochloride (2 eq., 5.1 g) in 250 mL of acetonitrile was heated to 80° C. for 2 days. The reaction mixture was then filtered, washed with CH2Cl2 (2.x.50 mL), and concentrated. The residue was dissolved in 200 mL of CH2Cl2, and washed with saturated NaHCO3, saturated NaCl, dried with Na2SO4 and concentrated. The residue was purified by ISCO graduate chromatography with 100percent CH2Cl2 to 5percent MeOH: 95percent CH2Cl2:0.5 mL of 2-aminopropane and then to 10percent MeOH: 90percent CH2Cl2:0.5 mL of 2-aminopropane to give the product. The product was dissolved in 15 mL of MeOH and then added 30 mL of 0.5 N HCl in EtOH. Evaporation of the solvent, and crystallization from MeOH:Et2O afforded the example 11 as the HCl salt (2.65 g, 41percent): Mp 240-2° C.; MS m/z 314 (M+H).
  • 6
  • [ 1005402-25-4 ]
  • [ 41720-98-3 ]
  • 5-Isopropyl-7-{4-[3-((R)-2-methyl-pyrrolidin-1-yl)-propoxy]-phenyl}-5H-thieno[2,3-d]pyridazin-4-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
A mixture of the product of step 4 (109 mg, 0.3 mmol), K2CO3 (3.5 eq, 145 mg), 50 mg of NaI, and R-2-methylpyrrolidine hydrochloride (1.2 eq., 44 mg) in 10 mL of acetonitrile was heated to 80° C. for 2 days. The reaction mixture was then filtered, washed with CH2Cl2 (2.x.20 mL) and concentrated. The residue was dissolved in 20 mL of CH2Cl2, and washed with saturated NaHCO3 solution, saturated NaCl solution, dried with Na2SO4, and concentrated. The residue was purified by preparative TLC or ISCO graduate silica gel chromatography (MeOH:CH2Cl2:2-aminopropane; 5:95:0.5) to give the product. The product was dissolved in 5 mL of MeOH, and added 0.5 mL of 1N HCl in EtOH. Evaporation of the solvent, and crystallization from MeOH:Et2O afforded the HCl salt of example 22 (5-isopropyl-7-(4-(3-((R)-2-methyl-pyrrolidin-1yl)propoxy)phenyl)-5H-thieno[2,3-d]pyridazin-4-one) (52 mg, 42percent): Mp 123-4° C.; MS m/z 412 (M+H).
  • 7
  • [ 1005402-33-4 ]
  • [ 41720-98-3 ]
  • 2,6-dimethyl-5-{4-[3-((R)-2-methylpyrrolidin-1-yl)propoxy]phenyl}-2H-pyridazin-3-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
A mixture of the product of step 3 (481 mg, 1.65 mmol), K2CO3 (3.5 eq, 795 mg), 50 mg of NaI, and R-2-methylpyrrolidine hydrochloride (2.0 eq., 773 mg) in acetonitrile (10 mL) was heated to 80° C. for 2 days. The reaction was then filtered, washed with CH2Cl2 (2.x.20 mL) and concentrated. The residue was dissolved in 30 mL of CH2Cl2 and washed with saturated NaHCO3, saturated NaCl solution, dried with Na2SO4 and then concentrated. The residue was purified by preparative TLC (10percent MeOH: 90percent CH2Cl2:0.5 mL 2-aminopropane) to give the product. The product was dissolved in 10 mL of MeOH, and was added 2.5 mL of 1N HCl in EtOH. The solvents were evaporated and the product crystallized from MeOH:Et2O to give example 86 as the HCl salt (231 mg, 41percent): Mp 176-8° C.; MS m/z 342 (M+H).
  • 8
  • [ 41720-98-3 ]
  • [ 627-30-5 ]
  • [ 862314-38-3 ]
YieldReaction ConditionsOperation in experiment
33% With potassium carbonate; potassium iodide; In butanone; at 100℃; To 3-chloro-1-propanol (1.00 g, 10.6 mmol) in 2-butanone (10.00 mL) was added R-2-methyl-pyrrolidine hydrochloride (1.93 g, 15.9 mmol), potassium carbonate (3.65 g, 26.44 mmol), and potassium iodide (1.76 g, 10.6 mmol). After overnight stirring at 100° C., the reaction was filtered, partitioned between dichloromethane/water, washed with brine, dried over sodium sulfate, and concentrated under vacuum to obtain 495 mg product (33percent); MS m/z 144 (M+H).
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