Trifluoroacetic acid → HCID 11951963, compound

HRID 2101509Notes

Reaction equation

HRID 2101509 reaction equation
C(OC(=O)[N:7]([C:16]1[N:17]([CH2:21][C:22]2[CH:27]=[C:26]([Cl:28])[CH:25]=[C:24]([Cl:29])[CH:23]=2)[CH:18]=[CH:19][N:20]=1)[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=1)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[Cl:29][C:24]1[CH:23]=[C:22]([CH:27]=[C:26]([Cl:28])[CH:25]=1)[CH2:21][N:17]1[CH:18]=[CH:19][N:20]=[C:16]1[NH:7][CH2:8][C:9]1[CH:10]=[CH:11][C:12]([F:15])=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57801499HCID 57801499, compound

Product 1

HCID 11951963HCID 11951963, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [1-(3,5-dichloro-benzyl)-1H-imidazol-2-yl]-(4-fluoro-benzyl)-carbamic acid tert-butyl ester in CH2Cl2 was added trifluoroacetic acid. The reaction solution was stirred at room temperature for 3 h. When all the starting material was consumed, the mixture was diluted with CH2Cl2 and washed with water. The organic phase was dried over Na2SO4 and concentrated. The resulting residue was purified by silica gel preparative TLC using CH2Cl2:MeOH 95:5 as an eluent to afford the title compound (24 mg, 63%); LCMS m/z 350 [C17H14Cl2FN3+H]+.

Workup

  1. customWhen all the starting material was consumed
  2. additionthe mixture was diluted with CH2Cl2
  3. washwashed with water
  4. dry with materialThe organic phase was dried over Na2SO4
  5. concentrationconcentrated
  6. customThe resulting residue was purified by silica gel preparative TLC

Sources & evidence

ORD record
ord-46f8cc0d51df4da88120d13691a9b078
Source dataset
uspto-grants-2009_08
Patent number
US07572921B2

Reaction notes

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