Trifluoroacetic acid → HCID 70937210, compound

HRID 1875250Notes

Reaction equation

HRID 1875250 reaction equation
CC([CH:5]([N:25]([C:29]([C:31]1[N:35](COCC[Si](C)(C)C)[CH:34]=[N:33][C:32]=1[Cl:44])=[O:30])C(=O)[O-])[C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[C:8]([O:13][C:14]2[CH:19]=[C:18]([CH2:20][OH:21])[CH:17]=[C:16]([C:22]#[N:23])[CH:15]=2)[C:7]=1[F:24])(C)C.[B-](F)(F)(F)F.[CH3:50]C[O+](CC)CC.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:44][C:32]1[N:33]([CH3:50])[CH:34]=[N:35][C:31]=1[C:29]([NH:25][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[C:8]([O:13][C:14]2[CH:19]=[C:18]([CH2:20][OH:21])[CH:17]=[C:16]([C:22]#[N:23])[CH:15]=2)[C:7]=1[F:24])=[O:30]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 2723982Triethyloxonium tetrafluoroborateHCID 86761666HCID 86761666, compound

Product 1

HCID 70937210HCID 70937210, compoundYield 76.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1,1-dimethylethyl[(4-chloro-3-{[3-cyano-5-(hydroxymethyl)phenyl]oxy}-2-fluorophenyl)methyl]{[4-chloro-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazol-5-yl]carbonyl}carbamate (66 mg, 0.099 mmol) in DCM (5 ml) was added Meerwein's reagent (16.13 mg, 0.109 mmol) and the reaction mixture was stirred for 4 hours at RT. TFA (2.0 ml, 26.0 mmol) was added and the reaction mixture was stirred at RT for another 2 hours. The solvent was removed and the crude material was purified via reverse phase HPLC to give the title compound (34 mg, 76% yield). 1H NMR (DMSO-d6) δ ppm 8.66 (t, 1H) 7.87 (s, 1H) 7.44-7.57 (m, 2H) 7.25-7.39 (m, 2H) 7.19 (s, 1H) 4.51 (s, 2H) 4.45 (d, 2 H) 2.50 (s, 3H). LC-MS (ES+) m/z 449.11 [M+H].

Workup

  1. stirringthe reaction mixture was stirred at RT for another 2 hours
  2. customThe solvent was removed
  3. customthe crude material was purified via reverse phase HPLC

Sources & evidence

ORD record
ord-272d647492a5419fa02e9ca8a629be44
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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