Triethylamine → 2-(methoxymethyl)-1H-thieno[3,4-d]imidazole

HRID 869589노트

반응식

HRID 869589 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.[CH3:18][O:19][CH2:20][C:21](=N)OCC.C(=O)([O-])O.[Na+]>C(O)C>[CH3:18][O:19][CH2:20][C:21]1[NH:3][C:4]2=[CH:5][S:6][CH:7]=[C:8]2[N:9]=1

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 127073423,4-Diaminothiophene dihydrochlorideHCID 12816254Ethyl 2-methoxyethanecarboximidate hydrochloride

생성물 1

HCID 867214402-(methoxymethyl)-1H-thieno[3,4-d]imidazole수율 58%

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 2-methoxyacetimidate monohydrochloride (Journal of Medicinal Chemistry, 1991, vol. 34, p 2468; 906 mg, 4.01 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-(methoxymethyl)-1H-thieno[3,4-d]imidazole (156 mg, 58%).

후처리

  1. addition906 mg, 4.01 mmol) were added
  2. extractionthe mixture was extracted 3 times with chloroform
  3. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. 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-4da503b96be44124a1bd2daaeaca8384
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08969345B2

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