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Chemical Structure| 3408-21-7 Chemical Structure| 3408-21-7

Structure of 3408-21-7

Chemical Structure| 3408-21-7

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Product Details of [ 3408-21-7 ]

CAS No. :3408-21-7
Formula : C10H14N2O
M.W : 178.23
SMILES Code : O=C(NNC(C)C)C1=CC=CC=C1
MDL No. :MFCD00463303

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Application In Synthesis of [ 3408-21-7 ]

* 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 [ 3408-21-7 ]

[ 3408-21-7 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 3408-21-7 ]
  • [ 1204-06-4 ]
  • [ 1407499-60-8 ]
YieldReaction ConditionsOperation in experiment
88% With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; at 20℃; for 12h; To solution containing (E)-3-(1H-indol-3-yl)acrylic acid (200 mg, 1.06 mmol), N?-isopropylbenzohydrazide (283.4 mg, 1.59 mmol) and HATU (604.6 mg, 1.59 mmol) dissolved in DMF (7.0 ml), N,N-diisopropylethylamine (DIPEA)(0.277 ml, 1.59 mmol) was slowly drop-wise added and stirred at room temperature for 12 hr. The reaction mixture was diluted with EtOAc, washed with water and brine, dried with anhydrous MgSO4, filtered, and concentrated under reduced pressure. The residue was separated through silica gel chromatography (n-hexane:EtOAc:methanol=15:3:1) and dried so that white solid form of (E)-N?-(3-(1H-indol-3-yl)acryloyl)-N?-isopropylbenzohydrazide was obtained (327 mg, 88%). [0284] 1H-NMR (DMSO, 500 MHz): delta 11.06 (brs, 1H, aromatic), 10.73 (brs, 1H, -N-NH-CO-), 7.98 (m, 2H, aromatic), 7.71 (m, 5H, aromatic), 7.41 (m, 2H, aromatic), 7.11 (m, 1H, aromatic), 6.87 (m, 1H, aromatic), 6.71 (d, J=15.65 Hz, indole-CH?CH-), 4.81 (m, 1H, -N-CH-(CH3)2), 1.18 (m, 6H, -N-CH-(CH3)2)
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; at 20℃; for 12h; General procedure: To a solution of the 4a (1g, 3.48 mmol), N'-isopropylbenzohydrazine (7a) (0.93g, 5.22 mmol) and HATU (1.98g,5.22 mmol) in DMF (15.0 mL) was added N,N-diisopropylethylamine (DIPEA) (0.90 ml, 5.22 mmol). The reaction mixture was then stirred at roomtemperature overnight, and then partitioned between ethyl acetate and water. Theorganic phase was washed with brine dried over MgSO4, andconcentrated. Purification by silica gel column chromatography using n-Hexane:EtOAc=3:1 as eluting solventsgave compound 8a as white solid.Compounds 8a-y, 14a-d, 15, 18, 20a and 20b were also prepared using same procedure.
 

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