Bromine → 4-[4-Methyl-2-(pyrazin-2-ylamino)-thiazol-5-yl]-benzenesulfonamide

HRID 908143Notes

Reaction equation

HRID 908143 reaction equation
BrBr.O=[C:4]([CH3:16])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([NH2:15])(=[O:14])=[O:13])=[CH:8][CH:7]=1.[N:17]1[CH:22]=[CH:21][N:20]=[CH:19][C:18]=1[NH:23][C:24]([NH2:26])=[S:25]>O1CCOCC1>[CH3:16][C:4]1[N:26]=[C:24]([NH:23][C:18]2[CH:19]=[N:20][CH:21]=[CH:22][N:17]=2)[S:25][C:5]=1[C:6]1[CH:11]=[CH:10][C:9]([S:12]([NH2:15])(=[O:14])=[O:13])=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 24408BromineHCID 2771013N-PyrazinylthioureaHCID 215301384-(2-Oxopropyl)benzene-1-sulfonamide

Product 1

HCID 99282444-[4-Methyl-2-(pyrazin-2-ylamino)-thiazol-5-yl]-benzenesulfonamideYield 28.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

Bromine (0.017 ml, 0.33 mmol) is added dropwise to a stirred solution of 4-(2-oxo-propyl)-benzenesulfonamide (prepared as described in European patent specification EP 91749 A2) (0.087 g, 4.1 mmol) in dioxan (10 ml) at 0° C. After 30 minutes the solvent is removed and the crude product is dissolved in ethanol (4.0 ml). Pyrazin-2-yl-thiourea (0.063 g, 0.41 mmol) is added and the stirred reaction mixture is heated at 60° C. for 3 hours. The solvent is removed and the residue is triturated with ethyl acetate to give the title compound as a pale orange solid (0.040 g). MH+ (AP+):

Workup

  1. customAfter 30 minutes the solvent is removed
  2. dissolutionthe crude product is dissolved in ethanol (4.0 ml)
  3. customthe stirred reaction mixture
  4. customThe solvent is removed
  5. customthe residue is triturated with ethyl acetate

Sources & evidence

ORD record
ord-25a701e0e72747c6bfc6b2da52dd6b31
Source dataset
uspto-grants-2011_09
Patent number
US08017608B2

Reaction notes

Loading…