Trifluoroacetic acid methylene chloride → HCID 46831172, compound

HRID 1667720Notes

Reaction equation

HRID 1667720 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:38]=[CH:37][C:18]3[N:19]=[CH:20][N:21]([C:22]4[S:23][C:24]([C:34](=[O:36])[NH2:35])=[C:25]([C:27]5[CH:32]=[CH:31][CH:30]=[C:29]([Cl:33])[CH:28]=5)[N:26]=4)[C:17]=3[CH:16]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.ClCCl.FC(F)(F)C(O)=O>ClCCl>[Cl:33][C:29]1[CH:28]=[C:27]([C:25]2[N:26]=[C:22]([N:21]3[C:17]4[CH:16]=[C:15]([O:14][CH:11]5[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]5)[CH:38]=[CH:37][C:18]=4[N:19]=[CH:20]3)[S:23][C:24]=2[C:34]([NH2:35])=[O:36])[CH:32]=[CH:31][CH:30]=1

Participants

4

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 67426381HCID 67426381, compound

Product 1

HCID 46831172HCID 46831172, compoundYield 61.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 0.10 g (0.18 mmole) of 4-{3-[5-carbamoyl-4-(3-chloro-phenyl)-thiazole-2-yl]-3H-benzoimidazol-5-yloxy}-piperidine-1-carboxylic acid tert-butyl ester (I.21a) 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 and washed with saturated aqueous sodium carbonate solution, brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was recrystallized from methanol to give 0.050 g 4-(3-chloro-phenyl)-2-[6-(piperidin-4-yloxy)-benzoimidazol-1-yl]-thiazole-5-carboxylic acid amide (I.21). MH+/Z=454

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionThe residue was diluted with dichloromethane
  3. washwashed with saturated aqueous sodium carbonate solution, 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-d77be21f5b6347e69d3ce4129b4abd30
Source dataset
uspto-grants-2011_10
Patent number
US08044213B2

Reaction notes

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