Sodium Hydroxide → HCID 86598716, compound

HRID 1593955Notes

Reaction equation

HRID 1593955 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([N:8]2[CH2:13][C@@H:12]3[CH2:14][C@H:9]2[CH2:10][N:11]3[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH:5]=[N:4][CH:3]=1.[Br:22]N1C(=O)CCC1=O.[OH-].[Na+]>C(#N)C>[Br:22][C:3]1[N:4]=[CH:5][C:6]([N:8]2[CH2:13][C@@H:12]3[CH2:14][C@H:9]2[CH2:10][N:11]3[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[N:7][C:2]=1[Cl:1]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 67184N-bromobutanimideHCID 86598715HCID 86598715, compound

Product 1

HCID 86598716HCID 86598716, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2-[6-chloro-2-pyrazinyl]-(1S,4S)-5-tert-butoxycarbonyl-2,5-diazabicyclo-[2.2.1]-heptane (10.6 g, 34.1 mmol), N-bromosuccinimide (6.06 g, 34.1 mmol) and acetonitrile (100 ml) was stirred for 3 hours. Aqueous sodium hydroxide (200 ml, 1 M) was added and the acetonitrile was evaporated. The mixture was extracted with ethyl acetate (2×200 ml). Chromatography on silica gel with ethyl acetate: petroleum (1:1) gave the title compound as free base. Yield 10.44 g (79%).

Workup

  1. customthe acetonitrile was evaporated
  2. extractionThe mixture was extracted with ethyl acetate (2×200 ml)

Sources & evidence

ORD record
ord-124bdac3dea647d5b8b1f59978192ad6
Source dataset
uspto-grants-2007_11
Patent number
US07300933B2

Reaction notes

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