Trifluoroacetic acid methylene chloride → HCID 46831174, compound

HRID 1667725Notes

Reaction equation

HRID 1667725 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][O:15][C:16]2[CH:39]=[CH:38][C:19]3[N:20]=[CH:21][N:22]([C:23]4[S:24][C:25]([C:35](=[O:37])[NH2:36])=[C:26]([C:28]5[CH:33]=[CH:32][CH:31]=[C:30]([Cl:34])[CH:29]=5)[N:27]=4)[C:18]=3[CH:17]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.ClCCl.FC(F)(F)C(O)=O>ClCCl>[Cl:34][C:30]1[CH:29]=[C:28]([C:26]2[N:27]=[C:23]([N:22]3[C:18]4[CH:17]=[C:16]([O:15][CH2:14][CH:11]5[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]5)[CH:39]=[CH:38][C:19]=4[N:20]=[CH:21]3)[S:24][C:25]=2[C:35]([NH2:36])=[O:37])[CH:33]=[CH:32][CH:31]=1

Participants

4

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 67428261HCID 67428261, compound

Product 1

HCID 46831174HCID 46831174, compoundYield 92.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 0.13 g (0.23 mmole) of 4-{3-[5-carbamoyl-4-(3-chloro-phenyl)-thiazole-2-yl]-3H-benzoimidazol-5-yloxymethyl}-piperidine-1-carboxylic acid tert-butyl ester (I.23a) in 5 mL of dichloromethane at 0 degrees, was added 5 mL of dichloromethane-trifluoroacetic acid (1:1). The mixture was stirred at 0 degrees for 1 hour and then concentrated under reduced pressure. The residue was diluted with dichloromethane, washed with saturated aqueous sodium carbonate solution and brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was recrystallized from methanol to give 0.10 g of 4-(3-chloro-phenyl)-2-[6-(piperidin-4-ylmethoxy)-benzoimidazol-1-yl]-thiazole-5-carboxylic acid amide (I.23). MH+/Z=468

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionThe residue was diluted with dichloromethane
  3. washwashed with saturated aqueous sodium carbonate solution and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was recrystallized from methanol

Sources & evidence

ORD record
ord-01787fa432f04e4297c25c97c7a5dca5
Source dataset
uspto-grants-2011_10
Patent number
US08044213B2

Reaction notes

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