HCID 86702385, compound → HCID 86702386, compound

HRID 1851245Notes

Reaction equation

HRID 1851245 reaction equation
[NH2:1][C:2]([C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([CH3:24])[N:19]=1)=[N:3][NH:4][C:5]([CH:7]1[CH2:10][N:9]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:8]1)=O>C(O)C>[CH3:24][C:20]1[N:19]=[C:18]([C:2]2[N:1]=[C:5]([CH:7]3[CH2:10][N:9]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:8]3)[NH:4][N:3]=2)[CH:23]=[CH:22][CH:21]=1

Participants

3

Reactant 1

HCID 86702385HCID 86702385, compound

Product 1

HCID 86702386HCID 86702386, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

16.4 g (49.3 mmol) tert-Butyl 3-({2-[amino(6-methylpyridine-2-yl)methylene]hydrazino}carbonyl)azetidine-1-carboxylate are heated under a nitrogen atmosphere to the melting point (220° C.) and kept there for 90 minutes. Ethanol is cautiously added to the reaction mixture during the cooling down phase (at around 135° C.). The reaction mixture is stirred over night at room temperature and the ethanol is evaporated. Due to an incomplete reaction the residue is heated once more to 220° C. for one hour and the work up is repeated yielding 12.91 g (74.58%) of the desired crude product (the byproduct is the cyclised compound which has lost the Boc group).

Workup

  1. customthe ethanol is evaporated
  2. customDue to an incomplete reaction the residue
  3. temperatureis heated once more to 220° C. for one hour

Sources & evidence

ORD record
ord-e2320281abda4a90afe668ffba273b47
Source dataset
uspto-grants-2015_02
Patent number
US08957064B2

Reaction notes

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