Hydrazine → HCID 178422070, compound

HRID 1040549Notes

Reaction equation

HRID 1040549 reaction equation
C([O:3][C:4](=O)[CH2:5][C:6]([C@@H:8]1[CH2:12][CH2:11][N:10]([C:13]([C:15]2([NH:18][C:19]([C:21]3[N:25]4[C@:26]([CH3:50])([CH2:38][C:39]5[CH:44]=[CH:43][C:42]([O:45][C:46]([F:49])([F:48])[F:47])=[CH:41][CH:40]=5)[C:27](=[O:37])[N:28]([C:29]5[CH:34]=[C:33]([Cl:35])[CH:32]=[C:31]([Cl:36])[CH:30]=5)[C:24]4=[N:23][CH:22]=3)=[O:20])[CH2:17][CH2:16]2)=[O:14])[CH2:9]1)=O)C.[NH2:52][NH2:53]>C(O)C>[Cl:35][C:33]1[CH:34]=[C:29]([N:28]2[C:27](=[O:37])[C@@:26]([CH3:50])([CH2:38][C:39]3[CH:44]=[CH:43][C:42]([O:45][C:46]([F:48])([F:47])[F:49])=[CH:41][CH:40]=3)[N:25]3[C:21]([C:19]([NH:18][C:15]4([C:13]([N:10]5[CH2:11][CH2:12][C@@H:8]([C:6]6[NH:53][N:52]=[C:4]([OH:3])[CH:5]=6)[CH2:9]5)=[O:14])[CH2:16][CH2:17]4)=[O:20])=[CH:22][N:23]=[C:24]23)[CH:30]=[C:31]([Cl:36])[CH:32]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 58431069HCID 58431069, compound

Product 1

HCID 178422070HCID 178422070, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 3-[(R)-1-(1-{[(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}-cyclopropanecarbonyl)-pyrrolidin-3-yl]-3-oxo-propionic acid ethyl ester (35 mg, 0.05 mmol) in ethanol (2 mL) was added hydrazine (7.0 μL, 0.23 mmol). The reaction mixture was stirred at room temperature for 1.5 h. The solvent was evaporated in vacuo, and the residue was purified via reverse phase HPLC to afford the title compound (20 mg, 60%) as a white solid, m/z 718.1 [M+1]+.

Workup

  1. customThe solvent was evaporated in vacuo
  2. customthe residue was purified via reverse phase HPLC

Sources & evidence

ORD record
ord-1a8eb85662c645658d19e4ba7b89d3a9
Source dataset
uspto-grants-2013_10
Patent number
US08552205B2

Reaction notes

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