Trifluoroacetic acid → HCID 178510243, compound

HRID 1875265Notes

Reaction equation

HRID 1875265 reaction equation
[Cl:1][C:2]1[C:7]([O:8][C:9]2[CH:10]=[C:11]([CH:15]=[C:16]([C:18]#[N:19])[CH:17]=2)[C:12]([OH:14])=[O:13])=[C:6]([F:20])[C:5]([CH2:21][NH:22][C:23]([C:25]2[N:29](COCC[Si](C)(C)C)[CH:28]=[N:27][C:26]=2[Cl:38])=[O:24])=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:1][C:2]1[C:7]([O:8][C:9]2[CH:10]=[C:11]([CH:15]=[C:16]([C:18]#[N:19])[CH:17]=2)[C:12]([OH:14])=[O:13])=[C:6]([F:20])[C:5]([CH2:21][NH:22][C:23]([C:25]2[NH:29][CH:28]=[N:27][C:26]=2[Cl:38])=[O:24])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68725206HCID 68725206, compound

Product 1

HCID 178510243HCID 178510243, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-({6-chloro-3-[({[4-chloro-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazol-5-yl]carbonyl}amino)methyl]-2-fluorophenyl}oxy)-5-cyanobenzoic acid (30 mg, 0.052 mmol) in DCM (2 ml) was added TFA (2 ml). The mixture was stirred for 30 min and the solvent was removed under vacuum. The crude product was purified by Reverse Phase HPLC (MeCN/water 0.1% formic acid) to give 20 mg (86%) of the title compound as a white solid. 1H NMR (400 MHz, methanol-d4) δ ppm 8.02 (s, 1H) 7.58-7.79 (m, 2H) 7.49 (d, 1H) 7.23-7.43 (m, 2H) 4.63 (s, 2H). LC-MS (ES+) m/z 448.10, [M+H].

Workup

  1. customthe solvent was removed under vacuum
  2. customThe crude product was purified by Reverse Phase HPLC (MeCN/water 0.1% formic acid)

Sources & evidence

ORD record
ord-55995510e776423a90ee1bc0474f3518
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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