Trifluoroacetic acid → HCID 178510917, compound

HRID 1875157Notes

Reaction equation

HRID 1875157 reaction equation
[Cl:1][C:2]1[N:3]=[CH:4][N:5](COCC[Si](C)(C)C)[C:6]=1[C:7]([NH:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([O:18][C:19]2[CH:24]=[C:23](/[CH:25]=[CH:26]/[C:27]#[N:28])[CH:22]=[C:21]([Cl:29])[CH:20]=2)[C:12]=1[F:30])=[O:8].C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:1][C:2]1[N:3]=[CH:4][NH:5][C:6]=1[C:7]([NH:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([O:18][C:19]2[CH:24]=[C:23](/[CH:25]=[CH:26]/[C:27]#[N:28])[CH:22]=[C:21]([Cl:29])[CH:20]=2)[C:12]=1[F:30])=[O:8]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 684855794-chloro-N-{[4-chloro-3-({3-chloro-5-[(E)-2-cyanoethenyl]phenyl}oxy)-2-fluorophenyl]methyl}-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazole-5-carboxamide

Product 1

HCID 178510917HCID 178510917, compoundYield 87.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-chloro-N-{[4-chloro-3-({3-chloro-5-[(E)-2-cyanoethenyl]phenyl}oxy)-2-fluorophenyl]methyl}-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazole-5-carboxamide (106 mg, 0.178 mmol) in DCM (5 ml) was added TFA (2.0 mL) and the reaction mixture was stirred at room temperature for 6 hours. The solvent was removed and the crude material was purified via reverse phase HPLC to give 4-chloro-N-{[4-chloro-3-({3-chloro-5-[(E)-2-cyanoethenyl]phenyl}oxy)-2-fluorophenyl]methyl}-1H-imidazole-5-carboxamide (72 mg, 0.155 mmol, 87% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 12.81-13.40 (m, 1H), 8.08-8.51 (m, 1H), 7.72 (s, 1H), 7.51-7.62 (m, 2H), 7.45 (d, 1H), 7.31 (t, 1H), 7.23 (s, 1H), 7.00 (s, 1H), 6.58 (d, 1H), 4.48 (d, 2H). LC-MS (ES+) m/z 464.94, [M+H].

Workup

  1. customThe solvent was removed
  2. customthe crude material was purified via reverse phase HPLC

Sources & evidence

ORD record
ord-ffa40efee0ea47629314bdd0b2cd866f
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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