Trifluoroacetic acid → HCID 178461130, compound

HRID 1875191Notes

Reaction equation

HRID 1875191 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]([F:28])([F:27])[CH3:26])[CH:22]=[C:21]([C:29]#[N:30])[CH:20]=2)[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]([F:27])([F:28])[CH3:26])[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 68484596HCID 68484596, compound

Product 1

HCID 178461130HCID 178461130, compoundYield 61.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-chloro-N-[(4-chloro-3-{[3-cyano-5-(1,1-difluoroethyl)phenyl]oxy}-2-fluorophenyl)methyl]-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazole-5-carboxamide (59 mg, 0.098 mmol) in DCM (6 ml) was added TFA (2.0 mL) and the reaction mixture was stirred at RT for 3 hours. The reaction mixture was purified via reverse phase HPLC to give 4-chloro-N-[(4-chloro-3-{[3-cyano-5-(1,1-difluoroethyl)phenyl]oxy}-2-fluorophenyl)methyl]-1H-imidazole-5-carboxamide (28 mg, 0.060 mmol, 61% yield). 1H NMR (400 MHz, METHANOL-d4) δ ppm 7.72 (s, 1H), 7.63 (s, 1H), 7.30-7.42 (m, 3H), 7.28 (s, 1H), 4.63 (s, 2H), 1.90 (t, 3H). LC-MS (ES+) m/z 469.08, [M+H].

Workup

  1. customThe reaction mixture was purified via reverse phase HPLC

Sources & evidence

ORD record
ord-dac9f234b3e74ef6bb10e11f3e3f752c
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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