Trifluoroacetic acid → HCID 178500964, compound

HRID 448000Notes

Reaction equation

HRID 448000 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-1cd283e530e043b29f425f28742ccd09
Source dataset
uspto-grants-2013_07
Patent number
US08481564B2

Reaction notes

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