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

HRID 78418

반응식

HRID 78418 반응식
[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]

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-82a0aa263bd64a1396aa0534c51643ff
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841334B2

연결된 노트

불러오는 중…