Bromine → [5-(4-Methanesulfonyl-3-trifluoromethyl-phenyl)-4-methyl-thiazol-2-yl]-pyrazin-2-yl-amine

HRID 908193Notes

Reaction equation

HRID 908193 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12](=O)[CH3:13])=[CH:7][C:6]=1[C:15]([F:18])([F:17])[F:16])(=[O:4])=[O:3].BrBr.[N:21]1[CH:26]=[CH:25][N:24]=[CH:23][C:22]=1[NH:27][C:28]([NH2:30])=[S:29]>O1CCOCC1.C(O)C>[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[S:29][C:28]([NH:27][C:22]3[CH:23]=[N:24][CH:25]=[CH:26][N:21]=3)=[N:30][C:12]=2[CH3:13])=[CH:7][C:6]=1[C:15]([F:18])([F:17])[F:16])(=[O:4])=[O:3]

Participants

6

Reactant 3

HCID 24408BromineHCID 2771013N-PyrazinylthioureaHCID 673910181-(4-Methanesulfonyl-3-trifluoromethyl-phenyl)-propan-2-one

Product 1

HCID 86606223[5-(4-Methanesulfonyl-3-trifluoromethyl-phenyl)-4-methyl-thiazol-2-yl]-pyrazin-2-yl-amine

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
10 °C

Procedure

1-(4-Methanesulfonyl-3-trifluoromethyl-phenyl)-propan-2-one (Example 59c) (0.60 g, 2.14 mmol) is dissolved in dioxan (50 ml) and the solution is cooled to 10° C. at which point the mixture is semi frozen. Bromine (0.088 ml, 1.7 mmol) is added slowly and the mixture is stirred for an additional 30 min in a semi frozen state. The mixture is then allowed to warm to room temperature and the solvent is removed to give a brown oil. This material is dissolved in ethanol and pyrazin-2-yl-thiourea (1a) is added in one portion. The mixture is stirred at 60° C. for 30 minutes then allowed to cool whereupon the titled product precipitates and is removed by filtration.

Workup

  1. temperatureis semi frozen
  2. temperaturefrozen state
  3. temperatureto warm to room temperature
  4. customthe solvent is removed
  5. customto give a brown oil
  6. stirringThe mixture is stirred at 60° C. for 30 minutes

Sources & evidence

ORD record
ord-ddff63fc334c420fb96dcb2389279267
Source dataset
uspto-grants-2011_09
Patent number
US08017608B2

Reaction notes

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