Triethylamine → Benzimidazole

HRID 1436188Notes

Reaction equation

HRID 1436188 reaction equation
[NH2:1][C@H:2](C(N)=O)[CH2:3][C:4]1C=CC(O)=C[CH:5]=1.Cl.C([N:17]([CH2:20]C)[CH2:18][CH3:19])C.FC(F)(F)C(OC1C(F)=C(F)C(F)=C(F)C=1F)=O>>[N:17]1[C:18]2[CH:19]=[CH:5][CH:4]=[CH:3][C:2]=2[NH:1][CH:20]=1

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 4327891Pentafluorophenyl TrifluoroacetateHCID 45157672L-Tyrosinamide--hydrogen chloride (1/1)

Product 1

HCID 5798BenzimidazoleYield 193.1%

Procedure

To a 0° C. crude solution of compound 2 (4.1 g, 15.34 mmol), triethylamine (6.4 mL, 46.02 mmol) in dicholoromethane (200 ml) was added pentafluorophenyl trifluoroacetate (6.35 mL, 36.82 mmol) via syringe over 3 mins. After 5 mins the ice bath was removed and the reaction mixture was stirred while warming to room temperature for another 2 hours. The reaction mixture was concentrated in vacuo. The resulting residue was purified by flash chromatography (silica gel, hexanes/ethyl acetate=1:0, 50:1) to give compound 3 (3.5 g, 50% yield).

Workup

  1. customAfter 5 mins the ice bath was removed
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customThe resulting residue was purified by flash chromatography (silica gel, hexanes/ethyl acetate=1:0, 50:1)

Sources & evidence

ORD record
ord-eb5723283982411297ad92764b379f1b
Source dataset
uspto-grants-2009_11
Patent number
US07618981B2

Reaction notes

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