Trifluoroacetic acid → HCID 178503477, compound

HRID 1874797Notes

Reaction equation

HRID 1874797 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][NH:16][C:17]([C:19]2[N:20]=[C:21]([S:43][CH3:44])[N:22](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH:23]=2)=[O:18])=[C:11]([F:45])[C:10]=1[O:46][C:47]1[CH:52]=[C:51]([C:53]#[N:54])[CH:50]=[C:49]([Cl:55])[CH:48]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][NH:16][C:17]([C:19]2[N:20]=[C:21]([S:43][CH3:44])[NH:22][CH:23]=2)=[O:18])=[C:11]([F:45])[C:10]=1[O:46][C:47]1[CH:52]=[C:51]([C:53]#[N:54])[CH:50]=[C:49]([Cl:55])[CH:48]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86644882HCID 86644882, compound

Product 1

HCID 178503477HCID 178503477, compoundYield 75.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-({4-chloro-3-[(3-chloro-5-cyanophenyl)oxy]-2-fluorophenyl}methyl)-2-(methylthio)-1-(triphenylmethyl)-1H-imidazole-4-carboxamide trifluoroacetate (0.030 g, 0.04 mmol) was dissolved in CH2Cl2 (2 mL) and trifluoroacetic acid (2 mL) and stirred for 2 h. The solvent was evaporated. Purification was accomplished by Reverse-Phase HPLC (water/acetonitrile with 0.1% TFA). The desired fractions were lyophilized to afford the title compound (0.017 g, 70%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ ppm 8.57 (t, 1H), 7.79 (s, 1H), 7.68 (s, 1H), 7.43-7.52 (m, 3H), 7.30 (t, 1H), 4.45 (d, 2H), 2.55 (s, 3H). MS: m/z 451.0 (M+1).

Workup

  1. customThe solvent was evaporated
  2. customPurification

Sources & evidence

ORD record
ord-8f4ea2bfef4c4906bf5c06fd27f5fb06
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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