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

HRID 340655Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 340655
[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]

Komponenten

5

Edukt 3

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

Produkt 1

HCID 86644543Methyl 5-isopropyl-2-{[2-fluoro-5-(trifluoromethyl)benzoyl]amino}-1,3-thiazole-4-carboxylateAusbeute 92,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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)+.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-90faabccc9a84e2ebb5d1565039fcaf5
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08895592B2

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