Hydrazine → HCID 10236834, compound

HRID 2105566Notes

Reaction equation

HRID 2105566 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8](/[CH:11]=[CH:12]/[C:13]([NH:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH2:23][CH2:24][N:25]3C(=O)C4C=CC=CC=4C3=O)[CH:17]=2)=[O:14])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].NN>CCO>[NH2:25][CH2:24][CH2:23][O:22][C:18]1[CH:17]=[C:16]([NH:15][C:13](=[O:14])/[CH:12]=[CH:11]/[C:8]2[CH:7]=[CH:6][C:5]([C:1]([CH3:3])([CH3:2])[CH3:4])=[CH:10][CH:9]=2)[CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 10195435HCID 10195435, compound

Product 1

HCID 10236834HCID 10236834, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a round-bottomed flask equipped with magnetic stirring was added Example 27, (2E)-3-[4-(tert-butyl)phenyl]-N-{3-[2-(1,3-dioxobenzo[c]azolin-2-yl)ethoxy]phenyl}prop-2-enamide, (856 mg, 1.83 mmol), EtOH (15 mL) and hydrazine (574 uL, 18.3 mmol, Aldrich). The reaction mixture was stirred at 25° C. for 2 h. The mixture was concentrated in vacuo, the residue dissolved in EtOAc (40 mL), washed with 10% K2CO3 (15 mL), water (15 mL), dried over Na2SO4, filtered and concentrated in vacuo. Purification by silica gel chromatography (step gradient, EtOAc followed by 1:1 EtOAc:EtOH) provided the title product as an oil. MS (ESI, pos. ion) m/z: 339 (M+1).

Workup

  1. customTo a round-bottomed flask equipped
  2. stirringThe reaction mixture was stirred at 25° C. for 2 h
  3. concentrationThe mixture was concentrated in vacuo
  4. dissolutionthe residue dissolved in EtOAc (40 mL)
  5. washwashed with 10% K2CO3 (15 mL), water (15 mL)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customPurification by silica gel chromatography (step gradient, EtOAc followed by 1:1 EtOAc:EtOH)

Sources & evidence

ORD record
ord-605029d74ef24d359dddfa465fc7e136
Source dataset
uspto-grants-2009_08
Patent number
US07579347B2

Reaction notes

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