Triethylamine → Methyl 5-isopropyl-2-{[2-fluoro-5-(trifluoromethyl)benzoyl]amino}-1,3-thiazole-4-carboxylate

HRID 340655Notes

Reaction equation

HRID 340655 reaction equation
[NH2:1][C:2]1[S:3][C:4]([CH:11]([CH3:13])[CH3:12])=[C:5]([C:7]([O:9][CH3:10])=[O:8])[N:6]=1.[F:14][C:15]1[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][C:16]=1[C:17](Cl)=[O:18].C(N(CC)CC)C>C(Cl)Cl>[CH:11]([C:4]1[S:3][C:2]([NH:1][C:17](=[O:18])[C:16]2[CH:20]=[C:21]([C:24]([F:25])([F:26])[F:27])[CH:22]=[CH:23][C:15]=2[F:14])=[N:6][C:5]=1[C:7]([O:9][CH3:10])=[O:8])([CH3:13])[CH3:12]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 737584Methyl 2-amino-5-(propan-2-yl)-1,3-thiazole-4-carboxylateHCID 27348802-Fluoro-5-(trifluoromethyl)benzoyl Chloride

Product 1

HCID 86644543Methyl 5-isopropyl-2-{[2-fluoro-5-(trifluoromethyl)benzoyl]amino}-1,3-thiazole-4-carboxylateYield 92.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of commercially available methyl 2-amino-5-isopropylthiazole-4-carboxylate (1 g, 4.99 mmol) and 2-fluoro-5-(trifluoromethyl)benzoyl chloride (1.31 g, 5 mmol) in anhydrous CH2Cl2 (25 mL) was treated dropwise at 0° C. with triethylamine (0.84 mL, 6 mmol). The mixture was allowed to warm to room temperature and stirred for 14 hours. The mixture was then washed with water, brine, dried with MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel chromatography and eluted with hexanes-EtOAc (1:1) to afford 1.8 g of the title compound. MS (DCI/NH3) m/z 391 (M+H)+.

Workup

  1. washThe mixture was then washed with water, brine
  2. dry with materialdried with MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel chromatography
  6. washeluted with hexanes-EtOAc (1:1)

Sources & evidence

ORD record
ord-90faabccc9a84e2ebb5d1565039fcaf5
Source dataset
uspto-grants-2014_11
Patent number
US08895592B2

Reaction notes

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