Water → N-[(5-bromo-1,3-thiazol-2-yl)carbamoyl]-4-(6-methoxypyridin-3-yl)-3-methylbenzenesulfonamide

HRID 252264

Reaction equation

HRID 252264 reaction equation
F[C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([S:14]([NH2:17])(=[O:16])=[O:15])=[CH:10][C:9]=2[CH3:18])=[CH:4][CH:3]=1.C(N(CC)CC)C.Cl[C:27](OC1C=CC=CC=1)=[O:28].[Br:36][C:37]1[S:41][C:40]([NH2:42])=[N:39][CH:38]=1.[CH3:43]S(O)(=O)=O.[OH2:48]>C(#N)C>[Br:36][C:37]1[S:41][C:40]([NH:42][C:43]([NH:17][S:14]([C:11]2[CH:12]=[CH:13][C:8]([C:5]3[CH:6]=[N:7][C:2]([O:28][CH3:27])=[CH:3][CH:4]=3)=[C:9]([CH3:18])[CH:10]=2)(=[O:16])=[O:15])=[O:48])=[N:39][CH:38]=1

Participants

8

Reactant 6

HCID 962WaterHCID 6395Methanesulfonic AcidHCID 8471TriethylamineHCID 15891Phenyl chloroformateHCID 436002-Thiazolamine, 5-bromo-HCID 668569644-(6-Fluoro-pyridin-3-yl)-3-methyl-benzenesulfonamide

Product 1

HCID 24752642N-[(5-bromo-1,3-thiazol-2-yl)carbamoyl]-4-(6-methoxypyridin-3-yl)-3-methylbenzenesulfonamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 4-(6-fluoro-pyridin-3-yl)-3-methyl-benzenesulfonamide (4.2 g, 16 mmol) and triethylamine (5.1 ml, 36.8 mmol, 2.3 equiv.) in 130 ml acetonitrile was added dropwise at 0° C. phenyl chloroformate (2.4 ml, 19.2 mmol, 1.2 equiv.) After stirring the solution for one hour at room temp., 5-bromo-thiazol-2-ylamine (4.3 g, 24 mmol, 1.5 equiv.) is added in one portion. The mixture was warmed to 60° C., then methanesulfonic acid (1.5 ml, 24 mmol, 1.5 equiv.) was added and the reaction mixture was stirred for one hour at 60° C. After cooling to room temp., the mixture was diluted with water and extracted with ethyl acetate. The combined organic extracts were washed with brine, dried over magnesium-dihydrate, filtered and evaporated. The crude product was purified on silica-gel with ethyl acetate/n-heptane to give 2.67 g of the title compound as a light brown solid. MS (ES): m/e 470.7 (M−H)

Workup

  1. stirringthe reaction mixture was stirred for one hour at 60° C
  2. temperatureAfter cooling to room temp.
  3. extractionextracted with ethyl acetate
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over magnesium-dihydrate
  6. filtrationfiltered
  7. customevaporated
  8. customThe crude product was purified on silica-gel with ethyl acetate/n-heptane

Sources & evidence

ORD record
ord-720dda439c0149b5952041bdbac68339
Source dataset
uspto-grants-2011_01
Patent number
US07868030B2

Linked notes

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