Triethylamine → Adamantane-1-carboxylic acid (5-chloro-thiazol-2-yl)-amide

HRID 255076

반응식

HRID 255076 반응식
[NH2:1][C:2]1[S:3][C:4]([Cl:7])=[CH:5][N:6]=1.[C:8]12([C:18](Cl)=[O:19])[CH2:17][CH:12]3[CH2:13][CH:14]([CH2:16][CH:10]([CH2:11]3)[CH2:9]1)[CH2:15]2.C(N(CC)CC)C>CN(C)C1C=CN=CC=1.C1COCC1.C(OCC)(=O)C>[Cl:7][C:4]1[S:3][C:2]([NH:1][C:18]([C:8]23[CH2:17][CH:12]4[CH2:11][CH:10]([CH2:16][CH:14]([CH2:13]4)[CH2:15]2)[CH2:9]3)=[O:19])=[N:6][CH:5]=1

참가 물질

7

반응물 3

HCID 8471TriethylamineHCID 389422-Amino-5-chlorothiazoleHCID 989151-Adamantanecarbonyl chloride

생성물 1

HCID 86619048Adamantane-1-carboxylic acid (5-chloro-thiazol-2-yl)-amide수율 51.3%

시약·촉매·용매 3

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

반응 조건

온도
80 °C

실험 절차

A mixture of 2-amino-5-chlorothiazole (2.00 g, 14.9 mmol), 1-adamantanecarbonyl chloride (3.54 g, 17.8 mmol), 4-dimethylaminopyridine (1.10 g, 0.90 mmol) and triethylamine (4.15 mL, 23.0 mmol) in 80 mL of THF was stirred at 80° C. for 48 hours The mixture was cooled to ambient temperature, diluted with 100 mL of ethyl acetate and washed with brine. The layers were separated and the aqueous phase was extracted twice with 50 mL of ethyl acetate. The combined organic extracts were dried over anhydrous Na2SO4, filtered, and concentrated. Purification by column chromatography (SiO2, dichloromethane) afforded 2.27 g of the title compound: MS (DCI/NH3) m/z 297 (M+H)+.

후처리

  1. temperaturewas cooled to ambient temperature
  2. washwashed with brine
  3. customThe layers were separated
  4. extractionthe aqueous phase was extracted twice with 50 mL of ethyl acetate
  5. dry with materialThe combined organic extracts were dried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification by column chromatography (SiO2, dichloromethane)

출처 및 근거

ORD 기록
ord-db9f264b210b4ee888b9dfde0a1eb5e9
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07875639B2

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