Hydrazine hydrate (1:1) → HCID 178462053, compound

HRID 456666Notes

Reaction equation

HRID 456666 reaction equation
[C:1]1([C@@H:7]([NH:9][C:10]([C:12]2[NH:13][C:14]([C:17]([C:19]3[C:20](Cl)=[N:21][CH:22]=[CH:23][CH:24]=3)=O)=[CH:15][CH:16]=2)=[O:11])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.[NH2:27][NH2:28]>C(O)C>[C:1]1([C@@H:7]([NH:9][C:10]([C:12]2[NH:13][C:14]([C:17]3[C:19]4[C:20](=[N:21][CH:22]=[CH:23][CH:24]=4)[NH:28][N:27]=3)=[CH:15][CH:16]=2)=[O:11])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 865922465-(2-chloro-pyridine-3-carbonyl)-1H-pyrrole-2-carboxylic acid ((S)-1-phenyl-ethyl)-amide

Product 1

HCID 178462053HCID 178462053, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 5-(2-chloro-pyridine-3-carbonyl)-1H-pyrrole-2-carboxylic acid ((S)-1-phenyl-ethyl)-amide (450 mg, 1.3 mmol) and hydrazine hydrate (2 mL) in ethanol (20 mL) was heated at 80° C. for 24 hours. The reaction was concentrated, the residue was triturated with water. The precipitate was collected by vacuum filtration, washed with water and DCM to give 80 mg (19%) of the titled compound.

Workup

  1. concentrationThe reaction was concentrated
  2. customthe residue was triturated with water
  3. filtrationThe precipitate was collected by vacuum filtration
  4. washwashed with water and DCM

Sources & evidence

ORD record
ord-565babc3f16c4edb957c95ea8e33f082
Source dataset
uspto-grants-2007_03
Patent number
US07186716B2

Reaction notes

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