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Chemical Structure| 50342-08-0

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Product Details of [ 50342-08-0 ]

CAS No. :50342-08-0
Formula : C4H7ClN2
M.W : 118.56
SMILES Code : ClCC1=NCCN1
MDL No. :MFCD06254248

Safety of [ 50342-08-0 ]

Application In Synthesis of [ 50342-08-0 ]

* 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 [ 50342-08-0 ]

[ 50342-08-0 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 50342-08-0 ]
  • [ 1776-37-0 ]
  • C12H14N4 [ No CAS ]
  • [ 1355356-65-8 ]
YieldReaction ConditionsOperation in experiment
27% General procedure: Sodium hydride (0.53 g, 6.6 mmol, 60percent oil dispresion) was added to the stirred solution of the corresponding azole (3.3 mmol) in anhydrous THF (2 mL) at room temperature. After 15 min, freshly prepared 2-(chloromethyl)-4,5-dihydro-1H-imidazole 2 (0.47 g, 4.0 mmol) was added and the reaction mixture was stirred at ambient temperature for 6 h. The N-alkylation products 3, 5, 7 and 8 were isolated upon quenching the reaction mixture with water (5 mL) followed by extraction with dichloromethane (3 .x. 5 mL). The combined organic layers were dried over anhydrous sodium sulfate and evaporated under reduced pressure. The oily residue thus obtained was purified on silica with use of chromatotron (Et3N/MeOH/AcOEt 1:5:100). All products were very polar with Rf values close to 0.05.The N-alkylation reaction of indazoles (1) provided the desired N1 substituted products (3) along with the N2 substituted side product. The latter compounds demonstrated considerably lower Rf than 3 and were not isolated in pure form. The alkylation reactions of benzotriazoles 6a and 6c allowed the isolation of N1 substituted products 7a-b (higher Rf) and N2 isomer 8b (lower Rf). However, in the case of 4-methyl-benzotriazole 6b only the N2 substituted isomer 8a was isolated as a pure product.The products 3, 5, 7 and 8 were then converted into water-soluble hydrochloride salts suitable for biological tests with use of methanolic hydrochloric acid solution or by passing gaseous hydrogen chloride through dichloromethane solution of the corresponding free base.
  • 2
  • [ 50342-08-0 ]
  • [ 37435-12-4 ]
  • [ 1355356-68-1 ]
  • C11H11ClN4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
34% General procedure: Sodium hydride (0.53 g, 6.6 mmol, 60% oil dispresion) was added to the stirred solution of the corresponding azole (3.3 mmol) in anhydrous THF (2 mL) at room temperature. After 15 min, freshly prepared 2-(chloromethyl)-4,5-dihydro-1H-imidazole 2 (0.47 g, 4.0 mmol) was added and the reaction mixture was stirred at ambient temperature for 6 h. The N-alkylation products 3, 5, 7 and 8 were isolated upon quenching the reaction mixture with water (5 mL) followed by extraction with dichloromethane (3 × 5 mL). The combined organic layers were dried over anhydrous sodium sulfate and evaporated under reduced pressure. The oily residue thus obtained was purified on silica with use of chromatotron (Et3N/MeOH/AcOEt 1:5:100). All products were very polar with Rf values close to 0.05.The N-alkylation reaction of indazoles (1) provided the desired N1 substituted products (3) along with the N2 substituted side product. The latter compounds demonstrated considerably lower Rf than 3 and were not isolated in pure form. The alkylation reactions of benzotriazoles 6a and 6c allowed the isolation of N1 substituted products 7a-b (higher Rf) and N2 isomer 8b (lower Rf). However, in the case of 4-methyl-benzotriazole 6b only the N2 substituted isomer 8a was isolated as a pure product.The products 3, 5, 7 and 8 were then converted into water-soluble hydrochloride salts suitable for biological tests with use of methanolic hydrochloric acid solution or by passing gaseous hydrogen chloride through dichloromethane solution of the corresponding free base.
  • 3
  • [ 50342-08-0 ]
  • [ 341-23-1 ]
  • 4-fluoro-1-[(4,5-dihydro-1H-imidazol-2-yl)methyl]-1H-indazole [ No CAS ]
  • C11H11FN4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
25% The title compounds were obtained according to a method described by J. Saczewski et al. [48]. To the stirred solution of properly substituted fluoroindazole (0.5 g, 3.7 mmol) in anhydrous THF (5 ml) sodium hydride (0.22 g, 5.5 mmol, 60% oil dispersion) was added in one portion. After 15 min freshly prepared 2-(chloromethyl)-4,5-dihydro-1H-imidazole was added and the reaction mixture was stirred at room temperature for 12 h. After this time the reaction was quenched with water (10 ml). The layers were separated and the aqueous one was extracted with dichloromethane (3 x10 ml). The combined organic layers were dried (Na2SO4) and evaporated under vacuum. The oily residue thus obtained was purified by preparative thin layer chromatography eluting first with ethyl acetate and then with ethyl acetate/methanol/triethylamine 50:5:3. The N1-alkylated products were eluted first, while the N2-alkylated ones had considerably lower Rf and were not isolated in pure form. Compounds 8a-8c were then converted into their hydrochloride salts 10a-10c by adding 1.5 molar equiv. of the ethereal solution of hydrochloride (2.6 M) to the solution of the appropriate fluoro-1-[(4,5-dihydro-1H-imidazol-2-yl)methyl]-1H-indazole in dichloromethane.
 

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