Trifluoroacetic acid → HCID 68512218, compound

HRID 1716594Notes

Reaction equation

HRID 1716594 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:18]3[CH:19]=[CH:20][C:21]([CH3:23])=[CH:22][C:17]=3[N:16]=[C:15]2[O:24][CH2:25][CH3:26])[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:25]([O:24][C:15]1[N:14]([CH:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)[C:18]2[CH:19]=[CH:20][C:21]([CH3:23])=[CH:22][C:17]=2[N:16]=1)[CH3:26]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68513365HCID 68513365, compound

Product 1

HCID 68512218HCID 68512218, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-(2-ethoxy-5-methylbenzoimidazol-1-yl)-piperidine-1-carboxylic acid tert-butyl ester (367 mg, 1.02 mmol) was dissolved in CH2Cl2 (2 mL) and TFA (1 mL) and the solution was stirred at rt for 1 hour. The mixture was evaporated to dryness and the residue was extracted with CH2Cl2, brine and 2N NaOH solution. The organic layer was washed with brine and dried over Na2SO4. After the evaporation of solvents, an oily residue was obtained (217 mg, 0.84 mmol) as 4-(2-ethoxy-5-methylbenzoimidazol-1-yl)-piperidine which was then was mixed with (S)-(2-iodomethyl-indan-5-yl)-carbamic acid tert-butyl ester (224 mg, 0.60 mmol) and cesium carbonate (817 mg, 2.51 mmol) in acetonitrile (10 mL). The mixture was stirred at 85° C. for 16 hrs. The reaction mixture was filtered and solvents were evaporated. The residue was purified through a Biotage flash column chromatography using 5% CH3OH in CH2Cl2 to give a brownish fluffy material (206 mg, 68%) as (S)-{2-[4-(2-ethoxy-5-methylbenzoimidazol-1-yl)-piperidin-1-ylmethyl]-indan-5-yl}-carbamic acid tert-butyl ester.

Workup

  1. customThe mixture was evaporated to dryness
  2. extractionthe residue was extracted with CH2Cl2, brine and 2N NaOH solution
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. customAfter the evaporation of solvents

Sources & evidence

ORD record
ord-4909e1dce3a6468a8150c65ec1bbfe0c
Source dataset
uspto-grants-2010_09
Patent number
US07803816B2

Reaction notes

Loading…