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Structure of 21377-09-3

Chemical Structure| 21377-09-3

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Product Details of [ 21377-09-3 ]

CAS No. :21377-09-3
Formula : C10H11N3
M.W : 173.21
SMILES Code : NC1=NN(CC2=CC=CC=C2)C=C1
MDL No. :MFCD03422517
InChI Key :VSUXHXCLAWFAJR-UHFFFAOYSA-N
Pubchem ID :1508616

Safety of [ 21377-09-3 ]

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

Application In Synthesis of [ 21377-09-3 ]

* 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 [ 21377-09-3 ]

[ 21377-09-3 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 1171919-75-7 ]
  • tert-butyl (3R)-3-[(2-sulfanylacetyl)amino]piperidine-1-carboxylate [ No CAS ]
  • [ 530-62-1 ]
  • [ 21377-09-3 ]
  • (R)-tert-butyl 3-(5-(1-benzyl-1H-pyrazol-3-yl)-4-oxo-4,5-dihydro-3H-1-thia-3,5,8-triazaacenaphthylene-2-carboxamido)piperidine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
58.85% To a 2-5 mL Biotage microwave vial with a stir bar were added 1 -benzyl- lH-pyrazol-3 -amine (132.7 mg, 0.766 mmol), 2-chloro- 4-iodonicotinonitrile (201 mg, 0.760 mmol), Pd(OAc)2(3.7 mg, 0.017 mmol), DPEPhos (12.5 mg, 0.0232 mmol), and CS2CO3(344 mg, 1.06 mmol). The vial was sealed, treated with dioxane (1.52 mL), evacuated/flushed with argon 4X, and stirred at 150 C under argon for 30. The reaction was then cooled to room temp, treated with fert-butyl (3R)-3-[(2- sulfanylacetyl)amino]piperidine-1-carboxylate (Intermediate 22) ( 1.2 mL, 0.65 M, 0.78 mmol) via syringe, evacuated/flushed with argon 4X, and stirred at 150 C for 15 min. The reaction was then cooled to room temperature, treated with solid CDI (492.6 mg, 3.038 mmol) in one portion under air, resealed and evacuated/flushed with argon 4X, and stirred at 150 C for 15 min. The reaction was diluted with EtOAc (10 mL), and washed with 0.5 M citric acid/brine (2 x 8 mL) and 2 M K2CO3(1 x 5 mL), dried over anhydrous Na2SC>4, filtered, and concentrated to dryness. The reaction mixture was purified by normal phase flash column chromatography (Si02) to give the title compound as an orange-yellow foam (256.6 mg, 58.85% yield).
  • 2
  • [ 1171919-75-7 ]
  • tert-butyl (3R)-3-[(2-sulfanylacetyl)amino]piperidine-1-carboxylate [ No CAS ]
  • [ 21377-09-3 ]
  • (R)-tert-butyl 3-(5-(1-benzyl-1H-pyrazol-3-yl)-4-oxo-4,5-dihydro-3H-1-thia-3,5,8-triazaacenaphthylene-2-carboxamido)piperidine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
58.85% To a 2-5 mL Biotage microwave vial with a stir bar were added 1-benzyl-1H-pyrazol-3-amine (132.7 mg, 0.766 mmol) , <strong>[1171919-75-7]2-chloro-4-iodonicotinonitrile</strong> (201 mg, 0.760 mmol) , Pd (OAc)2(3.7 mg, 0.017 mmol) , DPEPhos (12.5 mg, 0.0232 mmol) , and Cs2CO3(344 mg, 1.06 mmol) . The vial was sealed, treated with dioxane (1.52 mL) , evacuated/flushed with argon 4X, and stirred at 150 under argon for 30. The reaction was then cooled to room temp, treated with tert-butyl (3R) -3- [ (2-sulfanylacetyl) amino] piperidine-1-carboxylate (Intermediate 22) (1.2 mL, 0.65 M, 0.78 mmol) via syringe, evacuated/flushed with argon 4X, and stirred at 150 for 15 min. The reaction was then cooled to room temperature, treated with solid CDI (492.6 mg, 3.038 mmol) in one portion under air, resealed and evacuated/flushed with argon 4X, and stirred at 150 for 15 min. The reaction was diluted with EtOAc (10 mL) , and washed with 0.5 M citric acid/brine (2 x 8 mL) and 2 M K2CO3(1 x 5 mL) , dried over anhydrous Na2SO4, filtered, and concentrated to dryness. The reaction mixture was purified by normal phase flash column chromatography (SiO2) to give the title compound as an orange-yellow foam (256.6 mg, 58.85yield) .
 

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