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Chemical Structure| 124443-68-1 Chemical Structure| 124443-68-1

Structure of 124443-68-1

Chemical Structure| 124443-68-1

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CAS No.: 124443-68-1

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Product Details of [ 124443-68-1 ]

CAS No. :124443-68-1
Formula : C12H21NO4
M.W : 243.30
SMILES Code : O=C(N1CCC(C(OC)=O)CC1)OC(C)(C)C
MDL No. :MFCD02183584
InChI Key :PTZNCCIULVXFIJ-UHFFFAOYSA-N
Pubchem ID :392870

Safety of [ 124443-68-1 ]

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

Application In Synthesis of [ 124443-68-1 ]

* 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 [ 124443-68-1 ]

[ 124443-68-1 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 124443-68-1 ]
  • [ 13790-39-1 ]
  • [ 916730-84-2 ]
YieldReaction ConditionsOperation in experiment
100% With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 - 20℃; for 72h; c. 4-(6,7-Dimethoxy-quinazolin-4-yl)-piperidine-1,4-dicarboxylic acid 1-tert-butyl ester 4-methyl ester; To a mixture of piperidine-1,4-dicarboxylic acid 1-tert-butyl ester 4-methyl ester (17.1 g, 70.5 mmol), as prepared in the previous step, and <strong>[13790-39-1]4-chloro-6,7-dimethoxyquinazoline</strong> (15.0 g, 67.0 mmol) (Oakwood Products, Inc.) immersed in a -78 C. bath was added 1.08 M LiHMDS/THF (71 mL, 77 mmol) in 20 mL portions under argon via syringe along the sides of the flask (to allow cooling of the hindered base before reaction with the ester). Following completion of LiHMDS/THF addition, the reaction was allowed to sit in the -78 C. bath for 2-3 min before removing the cold bath and allowing the mixture to stir with gradual warming to rt. After 18 h stirring at rt, and an additional 2 d sitting at rt, the mixture was quenched with 0.5 M NaH2PO4 (150 mL) and extracted with DCM (1×150 mL and 1×100 mL). The organic layers were combined, dried (Na2SO4), and concentrated under reduced pressure to provide the crude title compound as a translucent yellow oil that was used in the next step without further purification (33 g, “114%” crude yield). A small sample was purified by flash chromatography (1:1 hex/EtOAc) for characterization. 1H-NMR (400 MHz, CDCl3) δ 9.11 (s, 1H), 7.34 (s, 1H), 7.29 (s, 1H), 4.05 (s, 3H), 3.96 (s, 3H), 3.76-3.67 (m, 2H), 3.62-3.49 (m, 2H), 3.61 (s, 3H), 2.50-2.36 (br s, 4H), 1.46 (s, 9H). LC/MS (ESI): calcd mass 431.2, found 432.2 (MH)+.
  • 2
  • [ 124443-68-1 ]
  • [ 16499-62-0 ]
  • [ 916731-79-8 ]
YieldReaction ConditionsOperation in experiment
100% With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 - 20℃; for 2.61667 - 2.63333h; EXAMPLE 65; 4-[7-(3-Methanesulfonylamino-propoxy)-quinazolin-4-yl]-piperidine-1-carboxylic acid (4-isopropoxy-phenyl)-amide; a. 4-(7-Fluoro-quinazolin-4-yl)-piperidine-1,4-dicarboxylic acid 1-tert-butyl ester 4-methyl ester; A mixture of 4-chloro-7-fluoro-quinazoline (2.87 g, 15.4 mmol) (WO 9609294 A1) and piperidine-1,4-dicarboxylic acid 1-tert-butyl ester 4-methyl ester (4.15 g, 17.1 mmol), as prepared in Example 1b, was placed in a -78 C. bath for 5 min under argon before adding a 1.08 M LiHMDS/THF solution (17.8 mL, 19.2 mmol) rapidly by syringe along the sides of the flask (to allow cooling and dispersion of the hindered base before reaction with the ester). Following completion of LiHMDS/THF addition, the reaction was manually swirled in the -78 C. bath for 2-3 min before removing the cold bath and allowing the mixture to stir with gradual warming to rt. After 2.5 h stirring at rt, the dark brown homogeneous solution was quenched with 1.0 M NaH2PO4 (38 mL) and extracted with DCM (1×150 mL and 1×25 mL). The organic layers were combined, dried (Na2SO4), and concentrated under reduced pressure, and subject to high vacuum at 90 C. with toluene chasers (3×10 mL) to provide the crude title compound as an opaque thick yellow oil that was used in the next step without further purification (6.83 g, “114%” crude yield). 1H-NMR (300 MHz, CDCl3) δ 9.26 (s, 1H), 8.11 (dd, 1H), 7.70 (dd, 1H), 7.36 (ddd, 1H), 3.74-3.64 (m, 2H), 3.62-3.51 (m, 2H), 3.61 (s, 3H), 2.47-2.38 (br m, 4H), 1.46 (s, 9H). LC/MS (ESI): calcd mass 389.2, found 390.1 (MH)+.
  • 3
  • [ 124443-68-1 ]
  • [ 1023595-19-8 ]
 

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