Hydrazine hydrate (1:1) → HCID 178451811, compound

HRID 1888207Notes

Reaction equation

HRID 1888207 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:24]#[N:25])[C:5](F)=[C:6]([C:8]([CH:10]2[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]2)=O)[CH:7]=1.O.[NH2:27][NH2:28]>C(O)C>[Br:1][C:2]1[CH:7]=[C:6]2[C:5](=[C:4]([C:24]#[N:25])[CH:3]=1)[NH:28][N:27]=[C:8]2[CH:10]1[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 59022871HCID 59022871, compound

Product 1

HCID 178451811HCID 178451811, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1,1-dimethylethyl 4-[(5-bromo-3-cyano-2-fluorophenyl)carbonyl]-1-piperidinecarboxylate (1.35 g, 3.3 mmols) and hydrazine hydrate (0.21 ml, 6.9 mmols) in ethanol (30 mL) was heated at reflux overnight. After cooling, the solvent was evaporated and the residue was purified by flash chromatography eluting with pentane/ethyl acetate 4:1 v/v to give the title compound (0.78 g) as a yellow solid (59%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. temperatureAfter cooling
  4. customthe solvent was evaporated
  5. customthe residue was purified by flash chromatography
  6. washeluting with pentane/ethyl acetate 4:1 v/v

Sources & evidence

ORD record
ord-df771e4b77904824b85a5327e4120681
Source dataset
uspto-grants-2013_08
Patent number
US08501780B2

Reaction notes

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