Trifluoroacetic acid → HCID 178509936, compound

HRID 1874799Notes

Reaction equation

HRID 1874799 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:9][C:10]([C:12]2[N:13]=[CH:14][N:15](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH:16]=2)=[O:11])=[C:4]([F:36])[C:3]=1[O:37][C:38]1[CH:43]=[C:42]([C:44]#[N:45])[CH:41]=[C:40]([Cl:46])[CH:39]=1.[C:47]([OH:53])([C:49]([F:52])([F:51])[F:50])=[O:48]>C(Cl)Cl>[F:50][C:49]([F:52])([F:51])[C:47]([OH:53])=[O:48].[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:9][C:10]([C:12]2[N:13]=[CH:14][NH:15][CH:16]=2)=[O:11])=[C:4]([F:36])[C:3]=1[O:37][C:38]1[CH:43]=[C:42]([C:44]#[N:45])[CH:41]=[C:40]([Cl:46])[CH:39]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59451514HCID 59451514, compound

Product 1

HCID 178509936HCID 178509936, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-({4-Chloro-3-[(3-chloro-5-cyanophenyl)oxy]-2-fluorophenyl}methyl)-1-(triphenylmethyl)-1H-imidazole-4-carboxamide (0.145 g, 0.22 mmol) was dissolved in CH2Cl2 (3 mL) and TFA (3 mL) added. The solution was stirred for 2.5 h. The solvent was evaporated. Purification was accomplished by Reverse-Phase HPLC (water/acetonitrile with 0.1% TFA) to afford the title compound (0.070 g, 60%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ ppm 9.01 (br. s., 1H), 8.53 (br. s., 1H), 7.94 (s, 1H), 7.83 (s, 1H), 7.45-7.54 (m, 4H), 7.38 (t, 1H), 4.54 (d, 2H). MS: m/z 405.0 (M+1).

Workup

  1. customThe solvent was evaporated
  2. customPurification

Sources & evidence

ORD record
ord-af8ebd343aa54eaf9ca0af79febe9aef
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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