Hydrazinecarboxaldehyde → HCID 54767655, compound

HRID 659627Notes

Reaction equation

HRID 659627 reaction equation
Cl.[CH2:2]([N:4]1[C:16]2[CH:15]=[CH:14][C:13]([CH2:17][N:18]3[CH2:23][CH2:22][CH2:21][CH:20]([C:24](=[NH:27])OC)[CH2:19]3)=[CH:12][C:11]=2[C:10]2[C:5]1=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH3:3].[CH:28]([NH:30][NH2:31])=O>N1C=CC=CC=1.O>[N:30]1[NH:31][C:24]([CH:20]2[CH2:21][CH2:22][CH2:23][N:18]([CH2:17][C:13]3[CH:14]=[CH:15][C:16]4[N:4]([CH2:2][CH3:3])[C:5]5[C:10]([C:11]=4[CH:12]=3)=[CH:9][CH:8]=[CH:7][CH:6]=5)[CH2:19]2)=[N:27][CH:28]=1

Participants

5

Reactant 2

HCID 12229HydrazinecarboxaldehydeHCID 67996332HCID 67996332, compound

Product 1

HCID 54767655HCID 54767655, compoundYield 1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Conditions

Temperature
110 °C

Procedure

A 100-mL round-bottomed flask was charged with a solution of methyl 1-((9-ethyl-9H-carbazol-3-yl)methyl)piperidine-3-carbimidate hydrochloride (1.44 g, 3.94 mmol, 1.00 equiv, 1.44%) in pyridine (20 mL) and formohydrazide (0.249 g, 4.07 mmol, 1.03 equiv, 0.249%). The resulting solution was stirred overnight at 110° C. in an oil bath. Upon completion, the resulting solution was cooled down to room temperature and diluted with water. This mixture was then extracted with ethyl acetate (3×30 mL). Combined organic layers were dried over anhydrous sodium sulfate. After filtration, organic later was concentrated on a rotary evaporator to give a residue that was purified by a silica gel column chromatography eluted with ethyl acetate/hexane (1:10) affording 3-((3-(2H-1,2,4-triazol-3-yl)piperidin-1-yl)methyl)-9-ethyl-9H-carbazole as white solid (0.011 g, 1%). LCMS: [M+H]+: 360. 1H NMR (CDCl3, 300 MHz) δ 11.55 (s, 1H), 8.10 (m, 3H), 7.68 (d, 1H), 7.50 (t, 1H), 7.38 (m, 2H), 7.25 (t, 1H), 4.35 (t, 3H), 3.76 (d, 2H), 3.50 (d, 1H), 2.66 (s, 1H), 2.32 (d, 1H), 2.12 (d, 1H), 2.01 (d, 1H), 1.84 (d, 1H), 1.55 (d, 1H), 1.39 (t, 3H).

Workup

  1. temperatureUpon completion, the resulting solution was cooled down to room temperature
  2. extractionThis mixture was then extracted with ethyl acetate (3×30 mL)
  3. dry with materialCombined organic layers were dried over anhydrous sodium sulfate
  4. filtrationAfter filtration
  5. concentrationorganic later was concentrated on a rotary evaporator
  6. customto give a residue that
  7. customwas purified by a silica gel column chromatography
  8. washeluted with ethyl acetate/hexane (1:10)

Sources & evidence

ORD record
ord-d53b2bb903ee4c909e875b22d45777ab
Source dataset
uspto-grants-2011_12
Patent number
US08080566B1

Reaction notes

Loading…