HCID 86655412, compound → N-[6-(3-aminophenoxy)-1H-benzimidazol-2-yl]cyclopropanecarboxamide

HRID 2190500Notes

Reaction equation

HRID 2190500 reaction equation
[CH:1]1([C:4]([NH:6][C:7]2[NH:11][C:10]3[CH:12]=[C:13]([O:16][C:17]4[CH:18]=[C:19]([NH:23]C(=O)OC(C)(C)C)[CH:20]=[CH:21][CH:22]=4)[CH:14]=[CH:15][C:9]=3[N:8]=2)=[O:5])[CH2:3][CH2:2]1>FC(F)(F)C(O)=O>[NH2:23][C:19]1[CH:18]=[C:17]([CH:22]=[CH:21][CH:20]=1)[O:16][C:13]1[CH:14]=[CH:15][C:9]2[N:8]=[C:7]([NH:6][C:4]([CH:1]3[CH2:3][CH2:2]3)=[O:5])[NH:11][C:10]=2[CH:12]=1

Participants

3

Reactant 1

HCID 86655412HCID 86655412, compound

Product 1

HCID 57388051N-[6-(3-aminophenoxy)-1H-benzimidazol-2-yl]cyclopropanecarboxamideYield 88.6%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

tert-Butyl [3-({2-[(cyclopropylcarbonyl)amino]-1H-benzimidazol-6-yl}oxy)phenyl]carbamate (1.58 g, 3.88 mmol) was suspended in trifluoroacetic acid (50 mL), and the reaction mixture was heated under reflux for 1 hr. The reaction mixture was cooled to room temperature, and concentrated under reduced pressure. The residue was diluted with ethyl acetate (200 mL), and washed with 0.1N hydrochloric acid (100 mL) and saturated aqueous sodium hydrogencarbonate solution (100 mL), successively. The collected aqueous layer was extracted with ethyl acetate (100 mL×2). The collected organic layer was dried over anhydrous magnesium sulfate, the insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The residue was recrystallized from methanol to give the title compound (1.06 g, 88%) as pale-brown crystals.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureunder reflux for 1 hr
  3. concentrationconcentrated under reduced pressure
  4. additionThe residue was diluted with ethyl acetate (200 mL)
  5. washwashed with 0.1N hydrochloric acid (100 mL) and saturated aqueous sodium hydrogencarbonate solution (100 mL)
  6. extractionThe collected aqueous layer was extracted with ethyl acetate (100 mL×2)
  7. dry with materialThe collected organic layer was dried over anhydrous magnesium sulfate
  8. filtrationthe insoluble material was filtered off
  9. concentrationthe filtrate was concentrated under reduced pressure
  10. customThe residue was recrystallized from methanol

Sources & evidence

ORD record
ord-84862bd47e7a4197b245be67337c0528
Source dataset
uspto-grants-2012_12
Patent number
US08324395B2

Reaction notes

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