Hydrazine → HCID 178464920, compound

HRID 1040526Notes

Reaction equation

HRID 1040526 reaction equation
C(O[C:4](=[O:51])[CH2:5][C:6]([C@@H:8]1[CH2:13][CH2:12][CH2:11][N:10]([C:14](=[O:50])[C@@H:15]([NH:17][C:18]([C:20]2[N:24]3[C@:25]([CH3:49])([CH2:37][C:38]4[CH:43]=[CH:42][C:41]([O:44][C:45]([F:48])([F:47])[F:46])=[CH:40][CH:39]=4)[C:26](=[O:36])[N:27]([C:28]4[CH:33]=[C:32]([Cl:34])[CH:31]=[C:30]([Cl:35])[CH:29]=4)[C:23]3=[N:22][CH:21]=2)=[O:19])[CH3:16])[CH2:9]1)=O)C.[NH2:52][NH2:53]>C(O)C>[Cl:34][C:32]1[CH:33]=[C:28]([N:27]2[C:26](=[O:36])[C@@:25]([CH3:49])([CH2:37][C:38]3[CH:39]=[CH:40][C:41]([O:44][C:45]([F:48])([F:47])[F:46])=[CH:42][CH:43]=3)[N:24]3[C:20]([C:18]([NH:17][CH:15]([CH3:16])[C:14]([N:10]4[CH2:11][CH2:12][CH2:13][C@@H:8]([C:6]5[NH:53][N:52]=[C:4]([OH:51])[CH:5]=5)[CH2:9]4)=[O:50])=[O:19])=[CH:21][N:22]=[C:23]23)[CH:29]=[C:30]([Cl:35])[CH:31]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 58430934HCID 58430934, compound

Product 1

HCID 178464920HCID 178464920, compoundYield 74.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 3-[(R)-1-((S)-2-{[(R)-7-(3,5-dichloro-phenyl)-5-methyl-6-oxo-5-(4-trifluoromethoxy-benzyl)-6,7-dihydro-5H-imidazo[1,2-a]imidazole-3-carbonyl]-amino}-propionyl)-piperidin-3-yl]-3-oxo-propionic acid ethyl ester (40 mg, 0.05 mmol) in ethanol (2 mL) was added hydrazine (8.5 μL, 0.26 mmol). The reaction mixture was stirred at room temperature for 1.5 h. The solvent was evaporated in vacuo, and the residue was purified using reverse phase HPLC to afford the title compound (27 mg, 71%) as a white solid, m/z 720.6 [M+1]+.

Workup

  1. customThe solvent was evaporated in vacuo
  2. customthe residue was purified

Sources & evidence

ORD record
ord-7d482164b4594b5b84f9688cd9e7e91e
Source dataset
uspto-grants-2013_10
Patent number
US08552205B2

Reaction notes

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