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Chemical Structure| 1306734-44-0 Chemical Structure| 1306734-44-0

Structure of 1306734-44-0

Chemical Structure| 1306734-44-0

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Product Details of [ 1306734-44-0 ]

CAS No. :1306734-44-0
Formula : C12H19NO4
M.W : 241.28
SMILES Code : O=C([C@H]1N(C(OC(C)(C)C)=O)[C@]2([H])C[C@]2(C)C1)O

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Application In Synthesis of [ 1306734-44-0 ]

* 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 [ 1306734-44-0 ]

[ 1306734-44-0 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 1306734-44-0 ]
  • [ 89466-16-0 ]
  • tert-butyl (1R,3S,5R)-3-((6-bromo-3-methylpyridin-2-yl)carbamoyl)-5-methyl-2-azabicyclo[3.1.0]hexane-2-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; In toluene; at 60℃; for 20h; (1R,3S,5R)-2-(tert-butoxycarbonyl)-5-methyl-2-azabicyclo[3.1.0]hexane-3-carboxylic acid (1 equiv), <strong>[89466-16-0]6-bromo-3-methylpyridin-2-amine</strong> (1.2 equiv), EEDQ (1.2 equiv) in toluene (10 vol) was stirred for 20h at 60 °C. The solvent was removed under reduced pressure and the remaining residue was dissolved in DCM ,Washed with IN HCl and washed with aq NaHCCb and dried over Na2S04. The solvent was removed and the residue was added to DCM/heptane (1 :3, 8 vol ) and stirred 10 min at RT and cooled to 5 °C. The precipitated solid was then filtered and directly used in the next reaction.
  • 2
  • [ 1306734-44-0 ]
  • [ 89466-16-0 ]
  • tert-butyl (1R,3S,5R)-3-((6-bromo-3-methylpyridin-2-yl)carbamoyl)-5-methyl-2-azabicyclo[3.1.0]hexane-2-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
595 mg With pyridine; trichlorophosphate; In dichloromethane; at 0℃; for 4h; (1R, 3S, 5R)-2-(tert-Butoxycarbonyl)- 5-methyl-2-azabicyclo[3. 1 .0]hexane-3 -carboxylic acid (15-51, 483mg, 2.0 mmol) and <strong>[89466-16-0]6-bromo-3-methylpyridin-2-amine</strong> (15-S2, 374mg, 2.Ommol) were dissolved in anhydrous DCM (l5mL). The reaction was cooled in an ice bath and dry pyridine (0.5mL, 6.Ommol) was added in one portion, followed by POC13 (2OOiL, 2.0 mmol). After completion of the addition, the mixture was stirred for 4 hours at 0°C, and the reaction was quenched with water (15 mL). The aqueous phase was extracted with DCM (1 5mLx2) and the combined organic layers was washed with brine driedover MgSO4. The solution was filtered and concentrated and the resulting residue was purified toafford 15-S3 (595 mg). ?H NMR (400 IVIFIz, DMSO-d6): (major rotamer) 0.61 (dd, J= 2.4, 5.3Hz, 1H), 0.68 (t,J= 5.6 Hz, 1H), 1.20 (s, 3H), 1.38 (s, 9H), 1.88-1.98 (m, 1H), 2.11 (s, 3H), 2.37-2.45 (m, 1H), 3.12 (s, 1H), 4.06 (dd, J 6.6, 8.9 Hz, 1H), 7.44 (d, J 7.9 Hz, 1H), 7.63 (d, J 7.9Hz, 1H), 10.17(s, 1H)ppm.
  • 3
  • [ 1306734-44-0 ]
  • [ 89466-16-0 ]
  • (1R,3S,5R)-2-(2-(3-acetyl-7-(hydroxymethyl)-5-(2-methylpyrimidin-5-yl)-1H-indazol-1-yl)acetyl)-N-(6-bromo-3-methylpyridin-2-yl)-5-methyl-2-azabicyclo[3.1.0]hexane-3-carboxamide [ No CAS ]
  • 4
  • [ 1158786-59-4 ]
  • [ 1306734-44-0 ]
  • (1R,3S,5R)-tert-butyl 3-((6-bromo-4-methoxypyridin-2-yl)carbamoyl)-5-methyl-2-azabicyclo[3.1.0]hexane-2-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
87.2% With pyridine; trichlorophosphate; In dichloromethane; at 0 - 20℃; for 2.0h;Inert atmosphere; To a mixture of compound 91- 1 (40 mg, 0.17 mmol) and compound 113-1 (6-Bromo-4-methoxy-pyridin-2-ylamine, 34 mg, 0.17 mmol) in DCM (5 mL) was added pyridine (67 mg, 0.85 mmol) followed by phosphoryl chloride (39 mg, 0.26 mmol) at 0 C, and the mixture was stirred at room temperature under N2 atmosphere for 2 hrs. The mixture was poured into ice water and extracted with DCM twice. The combined organic layers were washed with brine, dried with anhydrous Na2SO4, filtered, and concentrated to dryness. The residue was purified by chromatography on silica gel (PE: EtOAc= 30: 1 to 13: 1) to give compound 113-2 (63 mg, yield 87.2%) as a light oil. LC/MS (ESI) m/z: 426/428 (M+H)+.
 

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