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Chemical Structure| 1359656-11-3 Chemical Structure| 1359656-11-3

Structure of 1359656-11-3

Chemical Structure| 1359656-11-3

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Product Details of [ 1359656-11-3 ]

CAS No. :1359656-11-3
Formula : C6H12ClNO
M.W : 149.62
SMILES Code : C1NCC12OCCC2.[H]Cl
MDL No. :MFCD21364490
InChI Key :RVTZXQHPQGYYGT-UHFFFAOYSA-N
Pubchem ID :86280355

Safety of [ 1359656-11-3 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of [ 1359656-11-3 ]

* 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 [ 1359656-11-3 ]

[ 1359656-11-3 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 1354792-74-7 ]
  • [ 1359656-11-3 ]
  • [ 1419588-11-6 ]
YieldReaction ConditionsOperation in experiment
76% With sodium tris(acetoxy)borohydride; triethylamine; In dichloromethane; at 20.0℃; To a solution of 4-(1-(5-phenyl-1,3,4-oxadiazole-2-carbonyl)azetidin-3-yloxy)benzaldehyde (70 mg, 0.20 mmol) in dichloromethane (2 mL) was added <strong>[1359656-11-3]5-oxa-2-azaspiro[3.4]octane hydrochloride</strong> (80 mg, 0.53 mmol) and triethylamine (0.100 mL, 0.72 mmol). After stirring at ambient temperature for 30 minutes, sodium triacetoxyhydroborate (70 mg, 0.33 mmol) was added. Stirring was continued at ambient temperature overnight, after which NaHCO3 (aq, sat, 5ml) was added. The phases were separated with the aid of a phase separator. The aqueous phase was extracted twice with dichloromethane and dried with the aid of a phase separator. The combined organic phases were concentrated in vacuo to afford 88 mg of a colourless residue.The crude material was purified by preparative reverse-phase HPLC at pH 10 to give 68 mg (76 %) of the desired product as a solid.1H NMR (600 MHz, DMSO) delta 1.80 (p, 2H), 2.00 (t, 2H), 2.98 (d, 2H), 3.22 (dd, 2H), 3.51 (s, 2H), 3.65 (q, 2H), 4.09 (ddd, 1H), 4.53 - 4.57 (m, 1H), 4.63 (ddd, 1H), 5.10 (ddd, 1H), 5.15 (ddd, 1H), 6.84 (t, 2H), 7.23 (d, 2H), 7.68 (dtd, 3H), 8.08 (dd, 2H). MS (APCI+) m/z 447.2 [M+H]+, LC purity: 99 %
  • 2
  • [ 1354792-67-8 ]
  • [ 1359656-11-3 ]
  • [ 1419588-30-9 ]
YieldReaction ConditionsOperation in experiment
68% With sodium tris(acetoxy)borohydride; triethylamine; In dichloromethane; at 20.0℃; 5-Oxa-2-azaspiro[3.4]octane HCl salt (0.064 g, 0.43 mmol) was dissolved indichloromethane (2 ml). Triethylamine (0.064 ml, 0.47 mmol) was addded, followed by 2-methyl-4-(1-(5-phenyl-1,3,4-oxadiazole-2-carbonyl)azetidin-3-yloxy)benzaldehyde (0.13 g, 0.36 mmol) and finally sodium triacetoxyhydroborate (0.152 g, 0.72 mmol). The resulting mixture was stirred at ambient temperature overnight. The reaction mixture was the diluted with dichloromethane (10 ml) and shaken with NaHCO3 (sat. 3 ml). The two phases were separated by the use of a phase separator. Evaporation of the organic phase afforded a solid residue, which again was dissolved in dichloromethane (ca. 20 ml), washed with water (20 ml), filtered through a phase separator and evaporated. The residue was purified by column chromatography (ISOLUTE SI, 20g/70ml), eluting with NH3 in MeOH (2M)/dichloromethane (1 :99, 2:98). After evaporation of the solvent mixture, 112 mg (68 %) of the desired product was obtained as a solid. 1H NMR (400 MHz, CDC13) delta 1.91 (p, 2H), 2.14 (t, 2H), 2.33 (s, 3H), 3.15 (d, 2H), 3.39 (d, 2H), 3.59 (s, 2H), 3.82 (t, 2H), 4.35 (dd, 1H), 4.67 (dd, 1H), 4.74 - 4.8 (m, 1H), 5.11 (ddt, 2H), 6.57 (dd, 1H), 6.62 (d, 1H), 7.22 (d, 1H), 7.53 - 7.65 (m, 3H), 8.16 - 8.23 (m, 2H). MS (APCI+) m/z 461.3 [M+H]+, LC purity: 99 %
  • 3
  • [ 1254036-06-0 ]
  • [ 1359656-11-3 ]
  • [ 1419587-85-1 ]
YieldReaction ConditionsOperation in experiment
17% With sodium tris(acetoxy)borohydride; triethylamine; In dichloromethane; at 20.0℃; 5-Oxa-2-azaspiro[3.4]octane HC1 salt (0.052 g, 0.35 mmol) was dissolved indichloromethane (2 ml). Triethylamine (0.052 ml, 0.38 mmol) was added, followed by 4-(1-(5-(4-methoxyphenyl)-1,3,4-oxadiazole-2-carbonyl)azetidin-3-yloxy)benzaldehyde (0.11 g, 0.29 mmol) and finally sodium triacetoxyhydroborate (0.123 g, 0.58 mmol). The reaction was stirred at ambient temperature overnight. The reaction mixture was then diluted with dichloromethane (10 ml) and subsequently shaken with NaHCO3 (sat. 2 ml).The two phases were separated using a phase separator. The organic phase was evaporated. The product was purified by preparative reverse-phase HPLC at pH 10 to give 23 mg (17 %) of the desired product as a solid. 1H NMR (500 MHz, CDC13): delta 1.90 (p, 2H), 2.13 (t, 2H), 3.16 (d, 2H), 3.37 (d, 2H), 3.62 (s, 2H), 3.80 (t, 2H), 3.91 (s, 3H), 4.33 (dd, 1H), 4.62 - 4.7 (m, 1H), 4.73 - 4.78 (m, 1H), 5.03 - 5.16 (m, 2H), 6.74 (d, 2H), 7.04 (d, 2H), 7.25 (d, 2H), 8.11 (d, 2H). MS (APCI+) m/z 477.3 [M+H]+, LC purity: 97 %
  • 4
  • [ 1359656-11-3 ]
  • 5-chloro-2-[[5-methyl-3-(6-methyl-3-pyridyl)isoxazol-4-yl]methyl]pyridazin-3-one [ No CAS ]
  • 2-[[5-methyl-3-(6-methyl-3-pyridyl)isoxazol-4-yl]methyl]-5-(5-oxa-2-azaspiro[3.4]octan-2-yl)pyridazin-3-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
91% With potassium carbonate; In dimethyl sulfoxide; acetonitrile; at 70.0℃; for 18.0h; General procedure: To a stirred suspension of 5-chloro-2-[[5-methyl-3-(6-methyl-3-pyridyl)isoxazol-4- yl]methyl]pyridazin-3-one (building block A, 300 mg, 0.947 mmol) and (R)-3- hydroxypyrrolidine (0.14 mL, 1.73 mmol) in DMSO (0.5 mL) and acetonitrile (3 mL) was added potassium carbonate (393 mg, 2.84 mmol) Then the reaction mixture was stirred at 70 C for 18 h. After cooling to room temperature the reaction mixture was diluted with EtOAc (80 mL) was washed three times with water (10 mL) and brine (10 mL). The aqueous layers were back extracted twice with EtOAc (80 mL). The combined organic extracts were dried (Na2S04), filtered and concentrated in vacuo. Purification by flash chromatography (silica, gradient: 0% to 10% MeOH in CH2CI2) afforded the title compound (341 mg, 93 %) as an off-white foam. MS (ESI): 368.2 ([M+H]+).
 

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