Triethylamine → 2,2,3,3-Tetramethylcyclopropanecarboxylic acid (5-chloro-4-methyl-thiazol-2-yl)-amide

HRID 1037845

反応式

HRID 1037845 の反応式
[NH2:1][C:2]1(C)[NH:6][CH:5]=[C:4]([Cl:7])[S:3]1.[CH3:9][C:10]1([CH3:18])[C:12]([CH3:14])([CH3:13])[CH:11]1[C:15](Cl)=[O:16].[CH2:19](N(CC)CC)C>CN(C)C1C=CN=CC=1.C1COCC1.CCOC(C)=O>[Cl:7][C:4]1[S:3][C:2]([NH:1][C:15]([CH:11]2[C:10]([CH3:18])([CH3:9])[C:12]2([CH3:14])[CH3:13])=[O:16])=[N:6][C:5]=1[CH3:19]

参加物

7

反応物 3

HCID 8471TriethylamineHCID 110410022,2,3,3-Tetramethylcyclopropane-1-carbonyl chlorideHCID 686223502-Amino-5-chloro-2-methyl-thiazole

生成物 1

HCID 866189062,2,3,3-Tetramethylcyclopropanecarboxylic acid (5-chloro-4-methyl-thiazol-2-yl)-amide

試薬・触媒・溶媒 3

HCID 142844-(Dimethylamino)pyridine触媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A mixture of 2-amino-5-chloro-2-methyl-thiazole (Matsuo, Masaaki; Ogino, Takashi; Igari, Norihiro; Seno, Hachiro; Shimomura, Kyoichi, EP 412404) (150 mg, 0.81 mmol), 2,2,3,3-tetramethylcyclopropanecarbonyl chloride (143 mg, 0.89 mmol), 4-dimethylaminopyridine (50.0 mg, 0.41 mmol) and triethylamine (226 μL, 1.62 mmol) in 15 mL of THF heated at reflux for 48 hours. The mixture was cooled to ambient temperature, diluted with EtOAc and washed with brine. The layers were separated and the aqueous phase was extracted with EtOAc (2×). The combined organic extracts were dried (Na2SO4), filtered, and concentrated. Purification by silica gel chromatography afforded the title compound: MS (LC/MS) m/z 273 (M+H)+.

後処理

  1. temperatureheated
  2. temperatureat reflux for 48 hours
  3. washwashed with brine
  4. customThe layers were separated
  5. extractionthe aqueous phase was extracted with EtOAc (2×)
  6. dry with materialThe combined organic extracts were dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customPurification by silica gel chromatography

出典と根拠

ORDレコード
ord-9851936e0f8644ecafae11ecb839e968
出典データセット
uspto-grants-2013_10
特許番号
US08546583B2

関連ノート

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