Chlorosuccinimide → 3-Bromo-2-chloro-7-{[2-chloro-3-(trifluoromethyl)phenyl]carbonyl}-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine

HRID 1893427Notes

Reaction equation

HRID 1893427 reaction equation
[Br:1][C:2]1[N:6]2[CH2:7][CH2:8][N:9]([C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[C:14]=3[Cl:23])=[O:12])[CH2:10][C:5]2=[N:4][CH:3]=1.C1C(=O)N([Cl:31])C(=O)C1>CN(C)C=O>[Br:1][C:2]1[N:6]2[CH2:7][CH2:8][N:9]([C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:21])([F:22])[F:20])[C:14]=3[Cl:23])=[O:12])[CH2:10][C:5]2=[N:4][C:3]=1[Cl:31]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 497852023-Bromo-7-{[2-chloro-3-(trifluoromethyl)phenyl]carbonyl}-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine

Product 1

HCID 497853733-Bromo-2-chloro-7-{[2-chloro-3-(trifluoromethyl)phenyl]carbonyl}-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Bromo-7-{[2-chloro-3-(trifluoromethyl)phenyl]carbonyl}-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine (E18) (409 mg, 1 mmol) was dissolved in N,N-dimethylformamide (DMF) (5 mL) and NCS (147 mg, 1.100 mmol) was added. The solution was stirred at RT for 24 h. Solvents were removed in vacuo and the residue was purified by flash chromatography (Isolera, 25 g, 0-100% ethyl acetate/iso-hexane) to afford crude product. This was further purified by MDAP to afford desired product in 215 mg.

Workup

  1. customSolvents were removed in vacuo
  2. customthe residue was purified by flash chromatography (Isolera, 25 g, 0-100% ethyl acetate/iso-hexane)
  3. customto afford crude product
  4. customThis was further purified by MDAP

Sources & evidence

ORD record
ord-102d3a6a5b8748769e5fd217340b120c
Source dataset
uspto-grants-2013_08
Patent number
US08513248B2

Reaction notes

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