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Chemical Structure| 206193-17-1 Chemical Structure| 206193-17-1

Structure of 206193-17-1

Chemical Structure| 206193-17-1

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Product Details of [ 206193-17-1 ]

CAS No. :206193-17-1
Formula : C12H10BrF3N2O2
M.W : 351.12
SMILES Code : O=C(NC1=CC=C(C#N)C(C(F)(F)F)=C1)[C@@](C)(O)CBr
MDL No. :MFCD22200308

Safety of [ 206193-17-1 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319
Precautionary Statements:P501-P270-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330

Application In Synthesis of [ 206193-17-1 ]

* 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 [ 206193-17-1 ]

[ 206193-17-1 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 7126-38-7 ]
  • [ 206193-17-1 ]
  • (2S)-3-(3-cyano-1H-pyrrol-1-yl)-N-[4-cyano-3-(trifluoromethyl)phenyl]-2-hydroxy-2-methylpropanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
0.26 g (5)-3-(3-Cyano-lH-pyrrol-l-yl)-N-(4-cyano-3-(trifluoromethyl)phenyl)-2-hydroxy^ (0697) methylpropanamide (C17H13 (0698) (0699) [00318] To a solution of lH-<strong>[7126-38-7]pyrrole-3-carbonitrile</strong> (0.10 g, 0.00108 mol) in anhydrous THF (10 mL), which was cooled in an ice water bath under an argon atmosphere, was added sodium hydride (60percent dispersion in oil, 0.090 g, 0.00217 mol). After addition, the resulting mixture was stirred for 3 h. (7?)- 3-Bromo-N-(4-cyano-3-(trifluoromethyl)phenyl)-2-hydroxy-2-methylpropanamide (8, 0.38 g, 0.00108 mol) was added to above solution, and the resulting reaction mixture was allowed to stir overnight at RT under argon. The reaction was quenched by water, and extracted with ethyl acetate. The organic layer was washed with brine, dried with MgS04, filtered, and concentrated under vacuum. The product was purified by a silica gel column using ethyl acetate and hexanes (1 : 1) as eluent to afford 0.26 g of the titled compound as pinkish solid. (0700) [00319] Compound 1001 was characterized as follows: NMR (400 MHz, DMSO-i delta 10.44 (s, 1H, NH), 8.44 (s, 1H, ArH), 8.24 (d, = 8.8 Hz, 1H, ArH), 8.10 (d, = 8.8 Hz, 1H, ArH), 7.49 (s, 1H, Pyrrole-H), 6.38 (t, J = 2.0 Hz, 1H, Pyrrole-H), 6.41-6.40 (m, 2H, OH and Pyrrole-H), 4.30 (d, = 14.0 Hz, 1H, CH), 4.14 (d, = 14.0 Hz, 1H, CH), 1.34 (s, 3H, CH3); (ESI, Positive): 363.1079[M+H]+.
  • 2
  • [ 14521-81-4 ]
  • [ 206193-17-1 ]
  • (S)-N-(4-cyano-3-(trifluoromethyl)phenyl)-3-(3-fluoro-1H-pyrazol-1-yl)-2-hydroxy-2-methylpropanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
0.36 g (5)-N-(4-Cyano-3-(trifluoromethyl)phenyl)-3-(3-fluoro-lH-pyrazol- l-yl)-2-hydroxy-2- methylpropanamide Ci5Hi2F4N402 (1012) (0755) (0756) [00344] To a solution of 3-fluoro-pyrazole (0.20 g, 0.00232 mol) in anhydrous THF (10 mL), which was cooled in an ice water bath under an argon atmosphere, was added sodium hydride (60% dispersion in oil, 0.24 g, 0.00582 mol). After addition, the resulting mixture was stirred for 3 h. (7?)- 3-Bromo-N-(4-cyano-3-(trifluoromethyl)phenyl)-2-hydroxy-2-methylpropanamide (8, 0.82 g, 0.00232 mol) was added to above solution, and the resulting reaction mixture was allowed to stir overnight at RT under argon. The reaction was quenched by water, and extracted with ethyl acetate. The organic layer was washed with brine, dried with MgS04, filtered, and concentrated under vacuum. The product was purified by a silica gel column using ethyl acetate and hexanes (2: 1) as eluent to afford 0.36 g of the compound as white needles. (0757) [00345] Compound 1012 was characterized as follows: lH NMR (400 MHz, DMSO-i delta 10.39 (s, 1H, NH), 8.47 (d, = 2.0 Hz, 1H, ArH), 8.24 (dd, = 8.8 Hz, = 2.0 Hz, 1H, ArH), 8.11 (d, = 8.8 Hz, 1H, ArH), 7.55 (t, J = 3.0 Hz, 1H, Pyrazole-H), 6.29 (s, 1H, OH), 5.93-5.91 (m, 1H, Pyrazole- H), 4.34 (d, = 13.6 Hz, 1H, CH), 4.15 (d, = 13.6 Hz, 1H, CH), 1.36 (s, 3H, CH3); Mass (ESI, Positive): 357.0966 [M+H]+.
  • 3
  • [ 154258-82-9 ]
  • [ 206193-17-1 ]
  • (2S)-N-[4-cyano-3-(trifluoromethyl)phenyl]-3-[3-(4-fluorophenyl)-1H-pyrazol-1-yl]-2-hydroxy-2-methylpropanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
40% (5)-N-(4-Cyano-3-(trifluoromethyl)phenyl)-3-(3-(4-fluorophenyl)-lH-pyrazol- l-yl)-2-hydroxy- methylpropanamide (C21H16F4N4Q2) (1015) (0766) [00348] To a solution of 3-(4-fluorophenyl)-pyrazole (0.30 g, 0.00185 mol) in anhydrous THF (10 mL), which was cooled in an ice water bath under an argon atmosphere, was added sodium hydride (60% dispersion in oil, 0.22 g, 0.00555 mol). After addition, the resulting mixture was stirred for 3 h. ( ?)-3-Bromo-N-(4-cyano-3-(trifluoromethyl)phenyl)-2-hydroxy-2-methylpropanamide (8) (0.65 g, 0.00185 mol) was added to above solution, and the resulting reaction mixture was allowed to stir overnight at RT under argon. The reaction was quenched by water, and extracted with ethyl acetate. The organic layer was washed with brine, dried with MgS04, filtered, and concentrated under vacuum. The product was purified by a silica gel column using ethyl acetate and hexanes (2: 1) as eluent to afford 0.32 g (40%) of the titled compound as pinkish solid. (0767) [00349] Compound 1015 was characterized as follows: NMR (400 MHz, DMSO-i delta 10.30 (s, 1H, NH), 8.41 (d, = 2.0 Hz, 1H, ArH), 8.21 (dd, = 8.2 Hz, = 2.0 Hz, 1H, ArH), 8.05 (d, = 8.2 Hz, 1H, ArH), 7.68 (d, = 2.0 Hz, 1H, ArH), 7.64-7.59 (m, 2H, ArH), 7.11-7.05 (m, 2H, ArH), 6.65 (d, = 3.0 Hz, 1H, ArH), 6.31 (s, 1H, OH), 4.50 (d, = 13.6 Hz, 1H, CH), 4.30 (d, = 13.6Hz, 1H, CH), 1.42 (s, 3H, CH3); Mass (ESI, Positive): 433.1312 [M+H]+.
  • 4
  • [ 18225-90-6 ]
  • [ 206193-17-1 ]
  • (S)-N-(4-cyano-3-(trifluoromethyl)phenyl)-2-hydroxy-2-methyl-3-(5-fluoro-1H-benzo[d][1,2,3]triazol-1-yl)propanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
12.6% To a solution of <strong>[18225-90-6]5-fluoro-1H-benzo[d][1,2,3]triazole</strong> (0.20 g, 0.001459 mol) in anhydrous THF (5 mL), which was cooled in an ice water bath under an argon atmosphere, was added sodium hydride (60% dispersion in oil, 0.18 g, 0.004522 mol). After addition, the resulting mixture was stirred for three hours. (R)-3-Bromo-N-(4-cyano-3-(trifluoromethyl)phenyl)-2-hydroxy-2- methylpropanamide (8) (0.51 g, 0.001459 mol) was added to above solution, and the resulting reaction mixture was allowed to stir overnight at room temperature under argon. The reaction was quenched by water, and extracted with ethyl acetate. The organic layer was washed with brine, dried with MgSO4, filtered, and concentrated under vacuum. The product was purified by a silica gel column using hexanes and ethyl acetate (3:1 to 2:1) as eluent to afford 0.075 g (12.6%) of the titled compound as yellowish solid.1H NMR (400 MHz, DMSO-d6) d 10.35 (s, 1H, NH), 8.40 (s, 1H, ArH), 8.19 (d, J = 8.4 Hz, 1H, ArH), 8.10 (d, J = 8.0 Hz, 1H, ArH), 8.07-8.04 (m, 1H, ArH), 7.70 (d, J = 8.2 Hz, 1H, ArH), 7.28-6-7.23 (m, 1H, ArH), 6.45 (s, 1H, OH), 5.05 (d, J = 14.4 Hz, 1H, CH), 4.87 (d, J = 14.4 Hz, 1H, CH), 1.50 (s, 3H, CH3).Mass (ESI, Positive): 430.09 [M+Na]+.
 

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