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Chemical Structure| 74549-10-3 Chemical Structure| 74549-10-3

Structure of 74549-10-3

Chemical Structure| 74549-10-3

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Product Details of [ 74549-10-3 ]

CAS No. :74549-10-3
Formula : C8H7NO4
M.W : 181.15
SMILES Code : CC#CC(ON1C(CCC1=O)=O)=O

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Application In Synthesis of [ 74549-10-3 ]

* 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 [ 74549-10-3 ]

[ 74549-10-3 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 1420478-90-5 ]
  • [ 74549-10-3 ]
  • [ 1420477-60-6 ]
YieldReaction ConditionsOperation in experiment
86% In dichloromethane; at 0 - 5℃; for 0.9h; A thick suspension of the compound of Formula (5-A) (2.00 g, 4.99 mmol) in dichloromethane (40 mL) was cooled to 0-5 C. A solution of the compound of Formula (4-A) (0.90 g, 4.99 mmol) in dichloromethane (20 mL) was added to the suspension over 30 minutes. A clear, yellow solution resulted and stirring was continued at 0-5 C for 25 minutes when the reaction was deemed complete by TLC (aqueous work up of aliquot into dichloromethane, TLC solvent system: 3:7 methanol: ethyl acetate, Formula (5-A) rf = 0.05, Formula (1 ) rf = 0.45) and was allowed to warm to room temperature. The reaction solution was then washed with water (40 mL) and the organic layer was then separated, dried over anhydrous sodium sulfate, and concentrated in vacuo at 30-35 C to afford a yellow solid (2.49 g). The solid was then purified by column chromatography using ethyl acetate and methanol to afford Acalabrutinib (1 ) as a yellow solid (1 .99 g, 4.27 mmol, 86% yield).1H-NMR (DMSO-d6, 300 MHz; rotamers) delta: 1 .62 and 2.01 (3H, s (combined peaks)), 2.08-2.17 (1 H, m), 2.18-2.42 (2H, m), 3.31 (1 H, s), 3.51 - 3.69 (1 H, m), 3.82 (1 H, t, J = 6.5 Hz), 5.45-5.32 and 5.67-5.77 (1 H, each m), 6.14 and 6.20 (2H, each s), 7.14 (1 H, dd, J = 4.9 Hz, 1 1 .8 Hz), 7.18 (1 H, ddd, J = 0.9 Hz, 4.9 Hz, 7.32 Hz), 7.77-7.90 (4H, m), 8.16 (2H, dd, J = 1 .9 Hz, 8.37 Hz), 8.22 (1 H, d, J = 8.4 Hz), 8.41 (1 H, m), 10.85 (1 H, s).
 

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