Trifluoroacetic acid → HCID 178510246, compound

HRID 1875201Notes

Reaction equation

HRID 1875201 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]([C:25]#[N:26])[C:22]([F:27])=[CH:21][C:20]=2[N+:28]([O-:30])=[O:29])[C:12]=1[F:31])=[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]([C:25]#[N:26])[C:22]([F:27])=[CH:21][C:20]=2[N+:28]([O-:30])=[O:29])[C:12]=1[F:31])=[O:8]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68480655HCID 68480655, compound

Product 1

HCID 178510246HCID 178510246, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-chloro-N-({4-chloro-3-[(5-cyano-4-fluoro-2-nitrophenyl)oxy]-2-fluorophenyl}methyl)-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazole-5-carboxamide (78.0 mg, 0.085 mmol) in DCM (7 ml) was added TFA (3.0 mL) and the reaction mixture was stirred at RT for 2 hours. The solvent was removed and the crude material was purified via reverse phase HPLC to give 4-chloro-N-({4-chloro-3-[(5-cyano-4-fluoro-2-nitrophenyl)oxy]-2-fluorophenyl}methyl)-1H-imidazole-5-carboxamide (39 mg, 0.083 mmol, 98% yield). 1H NMR (400 MHz, METHANOL-d4) δ ppm 8.14 (d, 1H), 7.75 (s, 1H), 7.27-7.50 (m, 3H), 4.64 (s, 2H). LC-MS (ES+) m/z 468.07, [M+H].

Workup

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

Sources & evidence

ORD record
ord-7d05f4cc712a4f5cbcbcf84122a189a3
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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