Home Cart 0 Sign in  

[ CAS No. 1306734-44-0 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
Chemical Structure| 1306734-44-0
Chemical Structure| 1306734-44-0
Structure of 1306734-44-0 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 1306734-44-0 ]

Related Doc. of [ 1306734-44-0 ]

Alternatived Products of [ 1306734-44-0 ]

Product Details of [ 1306734-44-0 ]

CAS No. :1306734-44-0 MDL No. :
Formula : C12H19NO4 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 241.28 Pubchem ID :-
Synonyms :

Safety of [ 1306734-44-0 ]

Signal Word: Class:
Precautionary Statements: UN#:
Hazard Statements: Packing Group:

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   1~9

  • 1
  • [ 4072-67-7 ]
  • [ 1306734-44-0 ]
  • [ 1412815-47-4 ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 20℃; for 4h; To a suspension of Example 5, step d.2 (1.09 g, 4.52 mmol) and 1,1'- (biphenyl-4,4'-diyl)bis(2-bromoethanone) (0.869 g, 2.19 mmol) in acetonitrile (40 mL) was added DIEA (0.789 mL, 4.52 mmol), and the mixture was stirred at room temperature for 4 hrs. The volatile component was removed in vacuo, and the residue was partitioned between EtOAc (70 mL) and water (50 mL). The organic layer was washed with sat. NaHCC (50 mL), dried with Na2S04, evaporated in vacuo and dried under vacuum to give Example 5, step e (1.54 g) as white foam. 1H NMR (DMSO-d6, delta = 2.5 ppm, 400 MHz): 8.13 (d, J=8.3 Hz, 4H), 7.99 (d, J=8.5 Hz, 4H), 5.70-5.54 (m, 4H), 4.17 (m, 2H), 3.13-3.11 (m, 2H), 2.58-2.46 (m, 2H), 2.19 (m, 2H), 1.42-1.37 (two s, 18H), 1.24 (s, 6H), 0.76-0.70 (m, 4H). LC/MS: Anal. Calcd. for [M+Na]+ C40H48N2NaOio: 739.32; found: 739.52.
Example QC-19, step eTo a suspension oiExample QC-19 , step d.2 (1.09 g, 4.52 mmol) and 1, 1'- (biphenyl-4,4'-diyl)bis(2-bromoethanone) (0.869 g, 2.19 mmol) in acetonitrile (40 mL) was added DIEA (0.789 mL, 4.52 mmol), and the mixture was stirred at room temperature for 4 hrs. The volatile component was removed in vacuo, and the residue was partitioned between EtOAc (70 mL) and water (50 mL). The organic layer was washed with sat. aHC03 (50 mL), dried with Na2S04, evaporated in vacuo and dried under vacuum to give Example QC-19 , step e (1.54 g) as white foam. XH NMR (DMSO-d6, delta = 2.5 ppm, 400 MHz): 8.13 (d, J=8.3 Hz, 4H), 7.99 (d, J=8.5 Hz, 4H), 5.70-5.54 (m, 4H), 4.17 (m, 2H), 3.13-3.11 (m, 2H), 2.58-2.46 (m, 2H), 2.19 (m, 2H), 1.42-1.37 (two s, 18H), 1.24 (s, 6H), 0.76-0.70 (m, 4H). LC/MS: Anal. Calcd. for [M+Na C40H48N2NaOi0: 739.32; found: 739.52.
1.54 g With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 20℃; for 4h; To a suspension Example QC-19 , step d.2 (1.09 g, 4.52 mmol) and 1,1'- (biphenyl-4,4'-diyl)bis(2-bromoethanone) (0.869 g, 2.19 mmol) in acetonitrile (40 mL) was added DIEA (0.789 mL, 4.52 mmol), and the mixture was stirred at room temperature for 4 h. The volatile component was removed in vacuo, and the residue was partitioned between EtOAc (70 mL) and water (50 mL). The organic layer was washed with sat. NaHCO3 (50 mL), dried with Na2SO4, evaporated in vacuo and dried under vacuum to give Example QC-19 , step e (1.54 g) as white foam. 1H NMR (DMSO-d6, delta = 2.5 ppm, 400 MHz): 8.13 (d, J=8.3 Hz, 4H), 7.99 (d, J=8.5 Hz, 4H), 5.70-5.54 (m, 4H), 4.17 (m, 2H), 3.13-3.11 (m, 2H), 2.58-2.46 (m, 2H), 2.19 (m, 2H), 1.42-1.37 (two s, 18H), 1.24 (s, 6H), 0.76-0.70 (m, 4H). LC/MS: Anal. Calcd. for [M+Na]+ C40H48N2NaO10: 739.32; found: 739.52
  • 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
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.
  • 3
  • [ 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.
  • 4
  • [ 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 ]
  • 5
  • [ 4275-43-8 ]
  • [ 1306734-44-0 ]
  • tert-butyl (1R,3S,5R)-3-((1,3-diphenylpropan-2-yl)carbamoyl)-5-methyl-2-azabicyclo[3.1.0]hexane-2-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
76.4% With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 0 - 25℃; for 2h; 8.2 Step 2: tert-Butyl(1R,35,5R)-3-((1 ,3-diphenylpropan-2-yl)carbamoyl)-5-methyl-2-azabicycloj3.1.Ojhexane-2-carboxylate (3): To a mixture of 2 (70 mg, 0.33 mmol) and(1 R, 35, 5R)-2-(tert-butoxycarbonyl)-5 -methyl-2-azabicyclo[3. 1. 0]hexane-3 -carboxylicacid (88 mg, 0.36 mmol) in DMF (3 mL) was added DIPEA (86 mg, 0.66 mmol) and HATU(252 mg, 0.66 mmol) at 0 °C and the mixture was stirred at 25 °C for 2 hours. The mixture wasdiluted with ethyl acetate, washed with water and brine, dried over Na2SO4, filtered andconcentrated to dryness. The residue was purified by column chromatography via silica gel (elutedwith petroleum ether: EtOAc= 50: 1 to 1: 1) to afford compound 3 (110 mg, yield 76.4%) as colorless oil. LC/MS (ESI) m/z: 435(M+H)t
  • 6
  • [ 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)+.
  • 7
  • [ 1306734-44-0 ]
  • [ 17430-98-7 ]
  • tert-butyl (1R,3S,5R)-3-(((S)-1-cyclohexylethyl)carbamoyl)-5-methyl-2-azabicyclo[3.1.0]hexane-2-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; O‐(1H‐benzotriazol‐1‐yl)‐N,N,N′,N′‐tetramethyluronium tetrafluoroborate In N,N-dimethyl-formamide at 20℃; for 0.5h; Inert atmosphere; 1B.1 Step 1. tert-Butyl (1R,3S,5R)-3-(((S)-1-cyclohexylethyl)carbamoyl)-5-methyl-2- azabicyclo[3.1.0]hexane-2-carboxylate (72-1): To an ice-cold solution of compound 91-1 (0.1 g, 0.414 mmol,1 equiv.) and (1S)-1-cyclohexylethanamine (0.053 g, 0.414 mmol,1 equiv.) in DMF (2 mL) were added DIPEA (0.361 mL, 0.432 mmol,1 equiv.), and TBTU (0.153 g, 0.476 mmol,1.1 equiv.) successively. The cooling bath was removed and the reaction mixture was stirred at rt for 30 min. The solvent was removed under reduced pressure and the residue was dissolved in dichloromethane. The dichloromethane solution was washed successively with saturated aqueous sodium bicarbonate and cold 1N aqueous HCl. The organic layer was separated, dried (Na2SO4), and concentrated to give compound 72-1 as a colorless resin, which was used without further purification.
  • 8
  • [ 1214361-39-3 ]
  • [ 1306734-44-0 ]
  • C18H20BrF3N2O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
46.8% With pyridine; trichlorophosphate In dichloromethane at 0 - 20℃; for 3h; Inert atmosphere; 1.1 Step 1: To a mixture of intermediate 1 (100 mg, 0.41 mmol) and compound 1A (100 mg, 0.41 mmol) in DCM (5mL) was added pyridine (162 mg, 2.05 mmol), followed by addition of POCl3 (69 mg, 0.45 mmol) at 0 °C under N2 atmosphere. The mixture was stirred at room temperature for 3 hours. The mixture was poured into iced-water and extracted with DCM twice. The combined organic layer was washed with brine, dried over anhydrous Na2SO4, filtered and concentrated to dryness. The residue was purified by chromatography on silica gel (PE : EtOAc = 100: 1 to 5: 1) to give intermediate 2 (89 mg, yield 46.8%) as a white solid. LC/MS (ESI) m/z : 464 (M+H)+.
  • 9
  • [ 1214361-39-3 ]
  • [ 1306734-44-0 ]
  • C18H21BrF3N3O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
32.7% With pyridine; trichlorophosphate In dichloromethane at 0 - 35℃; for 4h; Inert atmosphere; 1.1 Step 1: To a mixture of intermediate 1 (100 mg, 0.42 mmol) and compound 1A (100 mg, 0.42 mmol) in DCM (8 mL) was added pyridine (164 mg, 2.07 mmol), followed by addition of POCl3 (70 mg, 0.45 mmol) at 0 °C under N2 atmosphere. The mixture was stirred at 35 °C for 4 hours. The mixture was cooled to 20 °C and poured into iced-water and extracted with DCM twice. The combined organic layer was washed with brine, dried over anhydrous Na2SO4, filtered and concentrated to dryness. The residue was purified by chromatography on silica gel (PE : EtOAc = 100: 1 to 5: 1) to give intermediate 2 (63 mg, yield 32.7%) as a white solid. LC/MS (ESI) m/z : 464 (M+H)+.
Same Skeleton Products
Historical Records