(R)-4-((R)-1-(5-bromo-1,2-dimethyl-1H-benzo[d]imidazol-7-yloxy)ethyl)-1-((R)-1-phenylethyl)pyrrolidin-2-one → (R)-4-((R)-1-(5-bromo-1,2-dimethyl-1H-benzo[d]imidazol-7-yloxy)ethyl)pyrrolidin-2-one

HRID 2209174Notes

Reaction equation

HRID 2209174 reaction equation
[Br:1][C:2]1[CH:12]=[C:11]([O:13][C@@H:14]([C@H:16]2[CH2:20][N:19]([C@@H](C3C=CC=CC=3)C)[C:18](=[O:29])[CH2:17]2)[CH3:15])[C:5]2[N:6]([CH3:10])[C:7]([CH3:9])=[N:8][C:4]=2[CH:3]=1>C(O)(C(F)(F)F)=O>[Br:1][C:2]1[CH:12]=[C:11]([O:13][C@@H:14]([C@H:16]2[CH2:20][NH:19][C:18](=[O:29])[CH2:17]2)[CH3:15])[C:5]2[N:6]([CH3:10])[C:7]([CH3:9])=[N:8][C:4]=2[CH:3]=1

Participants

3

Reactant 1

HCID 117843027(R)-4-((R)-1-(5-bromo-1,2-dimethyl-1H-benzo[d]imidazol-7-yloxy)ethyl)-1-((R)-1-phenylethyl)pyrrolidin-2-one

Product 1

HCID 117842972(R)-4-((R)-1-(5-bromo-1,2-dimethyl-1H-benzo[d]imidazol-7-yloxy)ethyl)pyrrolidin-2-one

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

(R)-4-((R)-1-(5-bromo-1,2-dimethyl-1H-benzo[d]imidazol-7-yloxy)ethyl)-1-((R)-1-phenylethyl)pyrrolidin-2-one in TFA (3 mL) was heated in a microwave reactor for 3 h at 140° C. The reaction mixture was then concentrated to give (R)-4-((R)-1-(5-bromo-1,2-dimethyl-1H-benzo[d]imidazol-7-yloxy)ethyl)pyrrolidin-2-one which was used for next step without further purification. LC/MS found for C15H18BrN3O2 as (M+H)+ 353.1.

Workup

  1. concentrationThe reaction mixture was then concentrated

Sources & evidence

ORD record
ord-0eda096ec4ee4483b4f990ce7cf1d165
Source dataset
uspto-grants-2016_06
Patent number
US09376441B2

Reaction notes

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