Triethylamine → N-(5-bromo-1,3-thiazol-2-yl)adamantane-1-carboxamide

HRID 1469956

반응식

HRID 1469956 반응식
Br.[NH2:2][C:3]1[S:4][C:5]([Br:8])=[CH:6][N:7]=1.[C:9]12([C:19](Cl)=[O:20])[CH2:18][CH:13]3[CH2:14][CH:15]([CH2:17][CH:11]([CH2:12]3)[CH2:10]1)[CH2:16]2.C(N(CC)CC)C>CN(C)C1C=CN=CC=1.C1COCC1.C(OCC)(=O)C>[Br:8][C:5]1[S:4][C:3]([NH:2][C:19]([C:9]23[CH2:18][CH:13]4[CH2:12][CH:11]([CH2:17][CH:15]([CH2:14]4)[CH2:16]2)[CH2:10]3)=[O:20])=[N:7][CH:6]=1

참가 물질

7

반응물 3

HCID 8471TriethylamineHCID 989151-Adamantanecarbonyl chlorideHCID 27238485-Bromothiazol-2-amine monohydrobromide

생성물 1

HCID 49760640N-(5-bromo-1,3-thiazol-2-yl)adamantane-1-carboxamide수율 65%

시약·촉매·용매 3

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

반응 조건

온도
80 °C

실험 절차

A mixture of 2-amino-5-bromothiazole monohydrobromide (3.00 g, 11.5 mmol), 1-adamantanecarbonyl chloride (2.74 g, 13.8 mmol), 4-dimethylaminopyridine (1.10 g, 0.90 mmol) and triethylamine (3.20 mL, 23.0 mmol) in 100 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, 20% ethyl acetate: 80% hexane) afforded 2.55 g of the title compound: 1H NMR (400 MHz, DMSO-d6) δ 1.67-1.72 (m, 6H) 1.92 (d, J=2.8 Hz, 6H) 1.97-2.04 (m, 3H) 7.55 (s, 1H) 11.50 (br m, 1H); MS (DCI/NH3) m/z 341 (M)+, 343 (M+2)+.

후처리

  1. temperatureThe mixture was 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, 20% ethyl acetate: 80% hexane)

출처 및 근거

ORD 기록
ord-36454baca6d94fa0851e651c9a5723aa
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09006275B2

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