Diethyl Ether → 1-(3-Amino-6-(4-(ethylsulfonyl)piperazin-1-yl)pyrazin-2-yl)-2-bromoethanone

HRID 1959378Notes

Reaction equation

HRID 1959378 reaction equation
[NH2:1][C:2]1[C:3]([C:19](=[O:21])[CH3:20])=[N:4][C:5]([N:8]2[CH2:13][CH2:12][N:11]([S:14]([CH2:17][CH3:18])(=[O:16])=[O:15])[CH2:10][CH2:9]2)=[CH:6][N:7]=1.[Br-:22].[Br-].[Br-].[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.CCOCC>CC(O)=O.Br>[NH2:1][C:2]1[C:3]([C:19](=[O:21])[CH2:20][Br:22])=[N:4][C:5]([N:8]2[CH2:9][CH2:10][N:11]([S:14]([CH2:17][CH3:18])(=[O:16])=[O:15])[CH2:12][CH2:13]2)=[CH:6][N:7]=1

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 21124087PyridiniumtribromideHCID 667446911-(3-Amino-6-(4-(ethylsulfonyl)piperazin-1-yl)pyrazin-2-yl)ethanone

Product 1

HCID 866620741-(3-Amino-6-(4-(ethylsulfonyl)piperazin-1-yl)pyrazin-2-yl)-2-bromoethanoneYield 11%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 260Hydrogen BromideSolvent

Procedure

A solution of 1-(3-amino-6-(4-(ethylsulfonyl)piperazin-1-yl)pyrazin-2-yl)ethanone (510 mg, 1.627 mmol) in AcOH (2 mL) and HBr in AcOH (0.5 mL of 33% w/v, 2.039 mmol) was treated with pyridinium tribromide (544.5 mg, 1.708 mmol) and the mixture allowed to stir at ambient temperature for 2 hours. The reaction was poured into ether (50 mL), partitioned between EtOAc/water and extract with EtOAc (3×). The mixture was dried (MgSO4), filtered, evaporated down and the resultant residue was purified on silica gel by flash column chromatography (0-100% EtOAc/Petrol) to afford the title compound as a orange oil (68 mg, 11% Yield). 1H NMR (400.0 MHz, DMSO) d 1.23 (t, 3H), 3.12 (q, 2H), 3.31 (m, 4H), 3.52 (m, 4H), 4.86 (s, 2H), 7.21 (s, 1H), 8.34 (s, 1H) ppm; MS (ES+) 393.91

Workup

  1. custompartitioned between EtOAc/water
  2. extractionextract with EtOAc (3×)
  3. dry with materialThe mixture was dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated down
  6. customthe resultant residue was purified on silica gel by flash column chromatography (0-100% EtOAc/Petrol)

Sources & evidence

ORD record
ord-bb3ed72726404527b658e0f0f01b36aa
Source dataset
uspto-grants-2013_04
Patent number
US08410112B2

Reaction notes

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