2-Aminothiazole → 2,2,3,3-tetramethyl-N-1,3-thiazol-2-ylcyclopropanecarboxamide

HRID 78395

반응식

HRID 78395 반응식
[NH2:1][C:2]1[S:3][CH:4]=[CH:5][N:6]=1.[CH3:7][C:8]1([CH3:16])[C:10]([CH3:12])([CH3:11])[CH:9]1[C:13](Cl)=[O:14].C(N(CC)CC)C>C(Cl)Cl.C(Cl)(Cl)Cl.O>[CH3:7][C:8]1([CH3:16])[C:10]([CH3:12])([CH3:11])[CH:9]1[C:13]([NH:1][C:2]1[S:3][CH:4]=[CH:5][N:6]=1)=[O:14]

참가 물질

7

반응물 3

HCID 21552-AminothiazoleHCID 8471TriethylamineHCID 110410022,2,3,3-Tetramethylcyclopropane-1-carbonyl chloride

생성물 1

HCID 7224802,2,3,3-tetramethyl-N-1,3-thiazol-2-ylcyclopropanecarboxamide수율 14%

시약·촉매·용매 3

HCID 962Water용매HCID 6212Chloroform용매HCID 6344Dichloromethane용매

반응 조건

온도
35 °C

실험 절차

To a solution of 2-aminothiazole (0.39 g, 3.9 mmol) in 10 mL of methylene chloride at 0° C. was added a solution of the product from Example 1A in 8 mL of chloroform, followed by triethylamine (1.0 mL, 7.7 mmol). The mixture was stirred for 7 hours at 35° C., cooled to ambient temperature and diluted with water. The phases were separated and the aqueous phase was extracted with methylene chloride. The combined organic extracts were washed twice with water and then brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. Purification by column chromatography (SiO2, 30-60% ethyl acetate/hexanes gradient) afforded 0.11 g (14%) of the title compound. 1H NMR (CDCl3, 300 MHz) δ ppm 1.18 (s, 1H), 1.25 (s, 6H), 1.35 (s, 6H), 6.92 (d, J=3.4 Hz, 1H), 7.39 (d, J=3.4 Hz, 1H), 10.7 (s, 1H); MS (DCI/NH3) m/z 225 (M+H)+. Anal. Calculated for C11H16N2OS: C, 58.90; H, 7.19; N, 12.49. Found: C, 59.03; H, 7.34; N, 12.34.

후처리

  1. temperaturecooled to ambient temperature
  2. customThe phases were separated
  3. extractionthe aqueous phase was extracted with methylene chloride
  4. washThe combined organic extracts were washed twice with water
  5. dry with materialbrine, dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customPurification by column chromatography (SiO2, 30-60% ethyl acetate/hexanes gradient)

출처 및 근거

ORD 기록
ord-816269fbd7084bc4a5013b91d290c72b
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841334B2

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