Water → 3-Bromo-5-(4-(isopropylsulfonyl)phenyl)pyrazin-2-amine

HRID 78293Notes

Reaction equation

HRID 78293 reaction equation
C1C(=O)N([Br:8])C(=O)C1.[CH:9]([S:12]([C:15]1[CH:20]=[CH:19][C:18]([C:21]2[N:22]=[CH:23][C:24]([NH2:27])=[N:25][CH:26]=2)=[CH:17][CH:16]=1)(=[O:14])=[O:13])([CH3:11])[CH3:10].O>CN(C=O)C.CCOC(C)=O>[Br:8][C:23]1[C:24]([NH2:27])=[N:25][CH:26]=[C:21]([C:18]2[CH:19]=[CH:20][C:15]([S:12]([CH:9]([CH3:11])[CH3:10])(=[O:13])=[O:14])=[CH:16][CH:17]=2)[N:22]=1

Participants

6

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 580843825-(4-(Isopropylsulfonyl)phenyl)pyrazin-2-amine

Product 1

HCID 580843723-Bromo-5-(4-(isopropylsulfonyl)phenyl)pyrazin-2-amine

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

NBS (1.926 g, 10.82 mmol) was added to a solution of 5-(4-isopropylsulfonylphenyl)pyrazin-2-amine (3 g, 10.82 mmol) in DMF at ambient temperature. The reaction mixture was stirred at ambient temperature for 30 min and then added to a rapidly stirring water (50 ml). The precipitate was filtered off and dried in vacuo. The solid obtained was slurried in EtOAc, filtered off and dried in vacuo to provide 3-bromo-5-(4-(isopropylsulfonyl)phenyl)pyrazin-2-amine used which was as such without further purification (8 g, 62%). 1H NMR (400.0 MHz, DMSO-d6) δ 8.80 (s, 1H), 8.2 (d, 2H), 7.90 (d, 2H), 7.2 (s, 2H), 3.4-3.5 (m, 1H), 1.20 (d, 6H); LC/MS m/z 358.0 [M+H]+.

Workup

  1. filtrationThe precipitate was filtered off
  2. customdried in vacuo
  3. customThe solid obtained
  4. filtrationfiltered off
  5. customdried in vacuo

Sources & evidence

ORD record
ord-c48dee1e11e04a029f5e3d2a0411c103
Source dataset
uspto-grants-2014_09
Patent number
US08841337B2

Reaction notes

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