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Chemical Structure| 69389-14-6 Chemical Structure| 69389-14-6

Structure of 69389-14-6

Chemical Structure| 69389-14-6

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Product Details of [ 69389-14-6 ]

CAS No. :69389-14-6
Formula : C13H15N3S
M.W : 245.34
SMILES Code : N1(C2=NC(C3=CC=CC=C3)=CS2)CCNCC1
MDL No. :MFCD03197046

Safety of [ 69389-14-6 ]

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

Application In Synthesis of [ 69389-14-6 ]

* 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 [ 69389-14-6 ]

[ 69389-14-6 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 401564-36-1 ]
  • [ 69389-14-6 ]
  • [ 401566-91-4 ]
YieldReaction ConditionsOperation in experiment
100% With sodium tris(acetoxy)borohydride; acetic acid; In 1,2-dichloro-ethane; at 20℃; for 13h; General procedure: To a solution of 22 (901 mg, 3.00 mmol), 4-phenyl-2-(piperazin-1-yl)thiazole(810 mg, 3.30 mmol) and acetic acid (0.17 mL, 3.0 mmol) in 1,2-dichloroethane (15 mL) was added sodium triacetoxyborohydride (1.27 g, 6.00 mmol) and the mixture stirred at room temperature for 13 h. The reaction mixture was poured into a saturated aqueous sodium hydrogen carbonate solution and extracted with chloroform. The extract was washed with brine, dried and concentrated under reduced pressure. The residue purified by silica gel chromatography with chloroform/methanol (30:1, v/v) to give 3-{(2S,4S)-1-tert-butoxycarbonyl-4-[4-(4-phenylthiazol-2-yl)piperazin-1-yl]pyrrolidin-2-ylcarbonyl}thiazolidine (1.59 g, 100%) as a pale yellow amorphous.1H NMR (300 MHz, CDCl3): delta 1.41, 1.46 (9H, s), 1.84-1.97 (1H, m), 2.40-2.73 (4H, m), 2.82-3.21 (4H, m), 3.34 (1H, t, J = 9.9 Hz), 3.47-4.13 (7H, m), 4.38-4.82 (3H, m), 6.78 (1H, s), 7.25 (1H, t, J = 7.1 Hz), 7.37 (2H, t, J = 7.1 Hz), 7.82 (2H, d, J = 7.1 Hz). To a solution of the above compound (1.59 g, 3.00 mmol) in ethyl acetate (6 mL) was added 4 mol/L hydrochloric acid in ethanol (7 mL), and the mixture stirred at room temperature for 12 h. The precipitated solid was collected by filtration to give the title compound (1.41 g, 83%) as a pale brown powder. Mp: >135 C; 1H NMR (300 MHz, DMSO-d6): delta 2.27-2.42 (1H, m), 2.95-3.18 (3H, m), 3.37-4.18 (16H, m), 4.47-4.78 (3H, m), 7.30 (1H, t, J = 7.3 Hz), 7.37-7.45 (3H, s), 7.87 (2H, d, J = 7.1 Hz), 9.17 (1H, br s), 10.93 (1H, br s); Anal. Calcd for C21H27N5OS2·33/10HCl·2/5C2H6O: C, 46.07; H,5.80; N, 12.32. Found: C, 45.84; H, 6.14; N, 11.93; LC-MS (ESI) m/z 430.4 [M+H]+.
 

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