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

HRID 869589

Reaction equation

HRID 869589 reaction equation
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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

[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%).

Workup

  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)

Sources & evidence

ORD record
ord-4da503b96be44124a1bd2daaeaca8384
Source dataset
uspto-grants-2015_03
Patent number
US08969345B2

Linked notes

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