Trifluoroacetic acid → HCID 178483263, compound

HRID 1875189Notes

Reaction equation

HRID 1875189 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]([CH2:25][N:26]([CH3:28])[CH3:27])[CH:22]=[C:21]([C:29]#[N:30])[CH:20]=2)[C:12]=1[F:31])=[O:8].[C:40]([OH:46])([C:42]([F:45])([F:44])[F:43])=[O:41]>C(Cl)Cl>[F:43][C:42]([F:45])([F:44])[C:40]([OH:46])=[O:41].[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]([CH2:25][N:26]([CH3:28])[CH3:27])[CH:22]=[C:21]([C:29]#[N:30])[CH:20]=2)[C:12]=1[F:31])=[O:8]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68488254HCID 68488254, compound

Product 1

HCID 178483263HCID 178483263, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-chloro-N-{[4-chloro-3-({3-cyano-5-[(dimethylamino)methyl]phenyl}oxy)-2-fluorophenyl]methyl}-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazole-5-carboxamide (82 mg, 0.138 mmol) in DCM (6.0 ml) was added TFA (2.00 mL) and the reaction mixture was stirred ar RT for one hour. The solvent was removed and the crude material was purified via reverse phase HPLC to give 4-chloro-N-{[4-chloro-3-({3-cyano-5-[(dimethylamino)methyl]phenyl}oxy)-2-fluorophenyl]methyl}-1H-imidazole-5-carboxamide trifluoroacetate (29 mg, 0.050 mmol, 36% yield). 1H NMR (400 MHz, METHANOL-d4) δ ppm 7.72 (s, 1H), 7.62 (s, 1H), 7.27-7.49 (m, 4H), 4.63 (s, 2H), 4.35 (s, 2H), 2.85 (s, 6H). LC-MS (ES+) m/z 462.08, [M+H].

Workup

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

Sources & evidence

ORD record
ord-d9fb1f179668454498a924cf55b3b555
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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