Trifluoroacetic acid → HCID 66740016, compound

HRID 1627309Notes

Reaction equation

HRID 1627309 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][S:15][C:16]2[N:17]([C:33]3[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=3)[C:18]([C:21]([C:24]3[CH:29]=[CH:28][C:27]([Cl:30])=[C:26]([O:31][CH3:32])[CH:25]=3)([CH3:23])[CH3:22])=[CH:19][N:20]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:30][C:27]1[CH:28]=[CH:29][C:24]([C:21]([C:18]2[N:17]([C:33]3[CH:34]=[CH:35][C:36]([F:39])=[CH:37][CH:38]=3)[C:16]([S:15][CH2:14][CH:11]3[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]3)=[N:20][CH:19]=2)([CH3:23])[CH3:22])=[CH:25][C:26]=1[O:31][CH3:32]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66740290HCID 66740290, compound

Product 1

HCID 66740016HCID 66740016, compoundYield 79.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 0° C. solution of tert-butyl-4-((5-(2-(4-chloro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-ylthio)methyl)piperidine-1-carboxylate (0.755 g, 1.31 mmol) in DCM (4 mL) was added TFA (1 mL). After stirring at room temperature 2 h, when the reaction was determined to be complete by LCMS, the reaction was concentrated in vacuo. The residue was diluted with DCM, washed with satd NaHCO3 and brine, dried over MgSO4 and concentrated in vacuo to afford 4-((5-(2-(4-chloro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-ylthio)methyl)piperidine (0.491 g) as a white solid. MS (ES): 474 [M+H]+.

Workup

  1. concentrationthe reaction was concentrated in vacuo
  2. additionThe residue was diluted with DCM
  3. washwashed with satd NaHCO3 and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-10fd9ea011ef4f9688d4ddb3ed33b64b
Source dataset
uspto-grants-2014_07
Patent number
US08785488B2

Reaction notes

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