N-bromobutanimide → tert-butyl ((1S,2S)-2-((3-bromo-5-(trifluoromethyl)pyrazin-2-yl)amino)cyclopentyl)carbamate

HRID 1750541Notes

Reaction equation

HRID 1750541 reaction equation
[F:1][C:2]([F:24])([F:23])[C:3]1[N:4]=[CH:5][C:6]([NH:9][C@H:10]2[CH2:14][CH2:13][CH2:12][C@@H:11]2[NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[N:7][CH:8]=1.[Br:25]N1C(=O)CCC1=O>C(Cl)Cl>[Br:25][C:5]1[C:6]([NH:9][C@H:10]2[CH2:14][CH2:13][CH2:12][C@@H:11]2[NH:15][C:16](=[O:22])[O:17][C:18]([CH3:20])([CH3:21])[CH3:19])=[N:7][CH:8]=[C:3]([C:2]([F:1])([F:23])[F:24])[N:4]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimide2×HCID 118308243HCID 118308243, compound

Product 1

HCID 118308064tert-butyl ((1S,2S)-2-((3-bromo-5-(trifluoromethyl)pyrazin-2-yl)amino)cyclopentyl)carbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl ((1S,2S)-2-((5-(trifluoromethyl)pyrazin-2-yl)amino)cyclopentyl)carbamate (3.49 g, 10.08 mmol) in dry DCM (67 ml) at 0° C. was added 1-bromopyrrolidine-2,5-dione (CAS number 128-08-5; 2.15 g, 12.09 mmol). The reaction was allowed to warm to room temperature overnight. A further portion of portion of 1-bromopyrrolidine-2,5-dione (CAS number 128-08-5; 1.70 g, 9.56 mmol) was added and the reaction stirred for an additional 24 hours. The reaction was concentrated in vacuo and then purified by column chromatography (silica, 0-30% ethyl acetate/petrol) to afford the title compound.

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. custompurified by column chromatography (silica, 0-30% ethyl acetate/petrol)

Sources & evidence

ORD record
ord-e5c695c3388c40389087ac2d888ca4fe
Source dataset
uspto-grants-2015_10
Patent number
US09156829B2

Reaction notes

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