Trifluoroacetic acid → HCID 178500964, compound

HRID 408941Notes

Reaction equation

HRID 408941 reaction equation
[CH3:1][O:2][C:3](=[O:39])[CH:4]([C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]([C:18]2[N:19](COCC[Si](C)(C)C)[CH:20]=[C:21]([C:23]#[N:24])[N:22]=2)=[O:17])=[C:11]([C:33]2[CH2:38][CH2:37][CH2:36][CH2:35][CH:34]=2)[CH:10]=1)[C:5]([O:7][CH3:8])=[O:6].C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:8][O:7][C:5](=[O:6])[CH:4]([C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]([C:18]2[NH:19][CH:20]=[C:21]([C:23]#[N:24])[N:22]=2)=[O:17])=[C:11]([C:33]2[CH2:38][CH2:37][CH2:36][CH2:35][CH:34]=2)[CH:10]=1)[C:3]([O:2][CH3:1])=[O:39]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59771303HCID 59771303, compound

Product 1

HCID 178500964HCID 178500964, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(4-{[4-cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carbonyl]-amino}-3-cyclohex-1-enyl-phenyl)-malonic acid dimethyl ester (as prepared in the previous step, 145 mg, 0.262 mmol) in 1.0 mL of DCM (CH2Cl2) was added 1.0 mL of TFA. After stirring at RT for 4 h, the mixture was concentrated in vacuo. The residue was purified by flash chromatography on silica gel (20-30% EtOAc-hexane) to give 93 mg (84%) of the title compound as a white solid: Mass spectrum (ESI, m/z): Calcd. for C22H22N4O5, 423.1 (M+H). found 422.8.

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. customThe residue was purified by flash chromatography on silica gel (20-30% EtOAc-hexane)

Sources & evidence

ORD record
ord-05dfadc7d1bc4099a0e8737407e1d056
Source dataset
uspto-grants-2014_06
Patent number
US08759347B2

Reaction notes

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