Bromide ion → 4-[2-(6-Chloro-pyrazin-2-ylamino)-4-methyl-thiazol-5-yl]-benzenesulfonamide

HRID 908144Notes

Reaction equation

HRID 908144 reaction equation
O=[C:2]([CH3:14])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH2:13])(=[O:12])=[O:11])=[CH:6][CH:5]=1.BrBr.[Cl:17][C:18]1[N:23]=[C:22]([NH:24][C:25]([NH2:27])=[S:26])[CH:21]=[N:20][CH:19]=1.[Br-]>O1CCOCC1.C(O)C>[Cl:17][C:18]1[N:23]=[C:22]([NH:24][C:25]2[S:26][C:3]([C:4]3[CH:9]=[CH:8][C:7]([S:10]([NH2:13])(=[O:12])=[O:11])=[CH:6][CH:5]=3)=[C:2]([CH3:14])[N:27]=2)[CH:21]=[N:20][CH:19]=1

Participants

7

Reactant 4

HCID 259Bromide ionHCID 24408BromineHCID 144606806-Chloropyrazin-2-ylthioureaHCID 215301384-(2-Oxopropyl)benzene-1-sulfonamide

Product 1

HCID 866062064-[2-(6-Chloro-pyrazin-2-ylamino)-4-methyl-thiazol-5-yl]-benzenesulfonamideYield 88.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 312751,4-DioxaneSolvent

Procedure

4-(2-Oxo-propyl)-benzenesulfonamide (prepared as described in European patent specification EP 91749 A2) (0.63 g, 2.9 mmol) is dissolved in dry dioxan (70 ml) at 0° C. and bromine (0.121 ml, 2.4 mmol) is added dropwise. The mixture is stirred for 45 minutes at room temperature then the solvent is removed in vacuo. 6-Chloro-pyrazin-2-yl-thiourea (0.35 g, 1.87 mmol) is added to a solution of the above bromide (0.546 g, 1.87 mmol) in ethanol and the solution is heated at 60° C. for 4 hours. The reaction mixture is allowed to cool and the solvent removed under vacuum to give the title compound (0.63 g). MH+ (ES+): 382.1, 384.2 (3:1)

Workup

  1. customthe solvent is removed in vacuo
  2. temperaturethe solution is heated at 60° C. for 4 hours
  3. temperatureto cool
  4. customthe solvent removed under vacuum

Sources & evidence

ORD record
ord-e6e64deabc564932a0b1722599bbbec6
Source dataset
uspto-grants-2011_09
Patent number
US08017608B2

Reaction notes

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