Trifluoroacetic acid → HCID 68467472, compound

HRID 131231Notes

Reaction equation

HRID 131231 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:38]([F:39])=[CH:37][C:17]3[N:18]=[C:19]([CH2:29][O:30][C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)[N:20]([CH2:21][C:22]4[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=4)[C:16]=3[CH:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O.C(=O)(O)[O-].[Na+]>O>[Cl:28][C:25]1[CH:26]=[CH:27][C:22]([CH2:21][N:20]2[C:16]3[CH:15]=[C:14]([N:11]4[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]4)[C:38]([F:39])=[CH:37][C:17]=3[N:18]=[C:19]2[CH2:29][O:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 68467496HCID 68467496, compound

Product 1

HCID 68467472HCID 68467472, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4.2 g of 4-[3-(4-chloro-benzyl)-6-fluoro-2-phenoxymethyl-3H-benzoimidazol-5-yl]-piperazine-1-carboxylic acid tert-butyl ester (7.6 mmol) were stirred in 50 ml trifluoroacetic acid (651 mmol) for 2 h at rt. The reaction mixture was diluted with 500 ml water and the pH adjusted to 8 with solid sodium bicarbonate and then to 9-10 with ammonium hydroxide, extracted with ethylacetate, washed with water and brine, dried over magnesium sulfate, filtered and concentrated in vacuo, leading to 3.34 g of 1-(4-chloro-benzyl)-5-fluoro-2-phenoxymethyl-6-piperazin-1-yl-1H-benzoimidazole as a light yellow solid (99%). MS(ISP): 451.2 (M+H)+.

Workup

  1. extractionto 9-10 with ammonium hydroxide, extracted with ethylacetate
  2. washwashed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bfb6469feb194e4c833c0b9eb3e92dbb
Source dataset
uspto-grants-2008_06
Patent number
US07384945B2

Reaction notes

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