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

HRID 340655

反応式

HRID 340655 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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)+.

後処理

  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)

出典と根拠

ORDレコード
ord-90faabccc9a84e2ebb5d1565039fcaf5
出典データセット
uspto-grants-2014_11
特許番号
US08895592B2

関連ノート

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