Triethylamine → 2-Methanesulfonylamino-4-(1-(2-fluoro-4-biphenylyl)ethyl)thiazole

HRID 2072725Notes

Reaction equation

HRID 2072725 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([CH:7]([C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[C:11]([F:21])[CH:10]=2)[CH3:8])[N:6]=1.C(N(CC)CC)C.[CH3:29][S:30](Cl)(=[O:32])=[O:31]>O1CCCC1.O>[CH3:29][S:30]([NH:1][C:2]1[S:3][CH:4]=[C:5]([CH:7]([C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)=[C:11]([F:21])[CH:10]=2)[CH3:8])[N:6]=1)(=[O:32])=[O:31]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 104699822-Amino-4-(1-(2-fluoro-4-biphenylyl)ethyl)thiazole

Product 1

HCID 156760492-Methanesulfonylamino-4-(1-(2-fluoro-4-biphenylyl)ethyl)thiazoleYield 71%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 2-amino-4-(1-(2-fluoro-4-biphenylyl)ethyl)thiazole (500 mg, 1.68 mmol) and triethylamine (340 mg, 3.36 mmol) in tetrahydrofuran was added methanesulfonyl chloride (385 mg, 3.36 mmol) by portion and the mixture was stirred at room temperature overnight. The reaction mixture was diluted with water, extracted with ethyl acetate and evaporated under reduced pressure to a residue, which was chromatographed and then recrystallized to afford 2-methanesulfonylamino-4-(1-(2-fluoro-4-biphenylyl)ethyl)thiazole (447 mg, 71% yield): mp 127.5°-129.0° C.

Workup

  1. extractionextracted with ethyl acetate
  2. customevaporated under reduced pressure to a residue, which
  3. customwas chromatographed
  4. customrecrystallized

Sources & evidence

ORD record
ord-cc098dd5a2244a92b066d6abd1baf686
Source dataset
uspto-grants-1990_04
Patent number
US04914112

Reaction notes

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