Triethylamine → 2-cyclopropyl-1H-thieno[3,4-d]imidazole

HRID 869591

반응식

HRID 869591 반응식
Cl.Cl.[NH2:3][C:4]1[C:8]([NH2:9])=[CH:7][S:6][CH:5]=1.C(N(CC)CC)C.Cl.[CH:18]1([C:21](=N)OCC)[CH2:20][CH2:19]1.C(=O)([O-])O.[Na+]>C(O)C>[CH:18]1([C:21]2[NH:3][C:4]3=[CH:5][S:6][CH:7]=[C:8]3[N:9]=2)[CH2:20][CH2:19]1

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 127073423,4-Diaminothiophene dihydrochlorideHCID 20026660Ethyl cyclopropanecarboximidate hydrochloride

생성물 1

HCID 867214422-cyclopropyl-1H-thieno[3,4-d]imidazole수율 32%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

[step 1] 3,4-Diaminothiophene dihydrochloride (300 mg, 1.60 mmol) was suspended in ethanol (12 mL), triethylamine (0.45 mL, 3.21 mmol) and ethyl cyclopropanecarboimidate monohydrochloride (WO200970485; 528 mg, 3.53 mmol) were added, and the mixture was stirred at room temperature for 70 hr. To the mixture was added saturated aqueous sodium hydrogen carbonate, and the mixture was extracted 3 times with chloroform. The combined organic layers were dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=100/0 v/v-0/100 v/v) to give 2-cyclopropyl-1H-thieno[3,4-d]imidazole (84 mg, 32%).

후처리

  1. extractionthe mixture was extracted 3 times with chloroform
  2. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=100/0 v/v-0/100 v/v)

출처 및 근거

ORD 기록
ord-90f81ebdcfc24a548bc469c7010c0eb5
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08969345B2

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