Picolinimidohydrazide → tert-butyl 4-[[(Z)-[amino(pyridin-2-yl)methylidene]amino]carbamoyl]piperidine-1-carboxylate

HRID 2048128Notes

Reaction equation

HRID 2048128 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([OH:16])=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(C1NC=CN=1)(C1NC=CN=1)=O.[N:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[C:35](=[N:37][NH2:38])[NH2:36]>ClCCl.O>[NH2:36]/[C:35](/[C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][N:29]=1)=[N:37]\[NH:38][C:14]([CH:11]1[CH2:10][CH2:9][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:13][CH2:12]1)=[O:16]

Participants

6

Reactant 3

HCID 70493PicolinimidohydrazideHCID 3928711-(tert-Butoxycarbonyl)-4-piperidinecarboxylic acidHCID 5250894Bis-(1H-imidazol-2-YL)-methanone

Product 1

HCID 87242610tert-butyl 4-[[(Z)-[amino(pyridin-2-yl)methylidene]amino]carbamoyl]piperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To as solution of 1-(tert-butoxycarbonyl)piperidine-4-carboxylic acid 37 g (167 mM) in dichloromethane (300 ml) is added carbonyl diimidazole (1 eq.) in small portion over a period of 30 min. pyridine-2-carbohydrazonamide is then added to reaction mixture and stirred at room temperature for 3 hrs. Dichloromethane is evauporated and reaction mass is then stirred in water for 30 min. solid precipitated is filtered and dried to afford the desired compound.

Workup

  1. additionis then added to reaction mixture
  2. customreaction mass
  3. customprecipitated
  4. filtrationis filtered
  5. customdried

Sources & evidence

ORD record
ord-dad7e00269a64eb1b53e22cce4d44df8
Source dataset
uspto-grants-2013_11
Patent number
US08592591B2

Reaction notes

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