N-bromobutanimide → 1-PIPERAZINECARBOXYLIC ACID, 4-(5-BROMOPYRAZINYL)-, 1,1-DIMETHYLETHYL ESTER

HRID 531453Notes

Reaction equation

HRID 531453 reaction equation
[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[N:7]1[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH2:8]1.[Br:20]N1C(=O)CCC1=O>C(Cl)(Cl)Cl>[Br:20][C:5]1[N:4]=[CH:3][C:2]([N:7]2[CH2:8][CH2:9][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:11][CH2:12]2)=[N:1][CH:6]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 21069279HCID 21069279, compound

Product 1

HCID 210692801-PIPERAZINECARBOXYLIC ACID, 4-(5-BROMOPYRAZINYL)-, 1,1-DIMETHYLETHYL ESTERYield 54.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Using similar reaction conditions as described in step i of intermediate 1, tert-butyl 4-(pyrazin-2-yl)piperazine-1-carboxylate (2 g, 7.5 mmol) was brominated with N-bromosuccinimide (1.46 g, 8.25 mmol) in chloroform (20 ml) to afford 1.4 g (54% yield) of the pure product. MS: m/z=343.1 (M+1).

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-3fac12a1f3b3427cac40720d71d24080
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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