Hydrazine → HCID 68776545, compound

HRID 1853396Notes

Reaction equation

HRID 1853396 reaction equation
[NH2:1][NH2:2].[CH2:3]1[CH:10]2[C:6]3([C:12]4[O:13][C:14](=O)[C:15]5[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=5[N:17]=4)[CH2:7][CH:8]([CH2:11][CH:4]1[CH2:5]3)[CH2:9]2>C1(C)C=CC=CC=1>[NH2:1][N:2]1[C:14](=[O:13])[C:15]2[C:16](=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:17]=[C:12]1[C:6]12[CH2:7][CH:8]3[CH2:11][CH:4]([CH2:3][CH:10]1[CH2:9]3)[CH2:5]2

Participants

4

Reactant 2

HCID 9321HydrazineHCID 68770928HCID 68770928, compound

Product 1

HCID 68776545HCID 68776545, compoundYield 99.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
22.5 °C

Procedure

Anhydrous hydrazine (0.30 mL, 9.56 mmol) was added to a solution of the product of Example 2A (0.79 g, 2.81 mmol) in toluene (10 mL). The solution was stirred at 20-25° C. for 10 hours, then diluted with toluene (15 mL) and heated at reflux under a Dean-Stark trap for 33 hours. The solution was cooled to room temperature and concentrated under vacuum to leave a white solid residue. The residue was purified by flash chromatography (silica gel, eluted with hexanes-EtOAc 70:30-50:50) to provide the title compound as a white solid (0.79 g, 72% yield). 1H NMR (300 MHz, CDCl3) δ ppm 1.64-1.78 (m, 4H), 2.05 (dd, J=10.5, 2.7 Hz, 2H), 2.08-2.18 (m, 2H), 2.40 (br s, 2H), 2.45-2.55 (m, 2H), 2.96 (t, J=6.6 Hz, 1H), 4.73 (s, 2H), 7.44 (ddd, J=8.1, 6.4, 1.7 Hz, 1H), 7.66-7.77 (m, 2H), 8.24 (ddd, J=8.0, 1.4, 0.7 Hz, 1H); MS (DCI) m/z 282 (M+H)+.

Workup

  1. temperatureheated
  2. temperatureat reflux under a Dean-Stark trap for 33 hours
  3. temperatureThe solution was cooled to room temperature
  4. concentrationconcentrated under vacuum
  5. customto leave a white solid residue
  6. customThe residue was purified by flash chromatography (silica gel, eluted with hexanes-EtOAc 70:30-50:50)

Sources & evidence

ORD record
ord-a503f8e812584d6b977f33190237bb2c
Source dataset
uspto-grants-2015_02
Patent number
US08962639B2

Reaction notes

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