Benzene → HCID 59251258, compound

HRID 1466432Notes

Reaction equation

HRID 1466432 reaction equation
[F:1][C:2]([F:36])([F:35])[CH2:3][NH:4][C:5]([C:7]1[N:8]=[C:9]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[Cl:34])[N:10]([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([S:24]([CH3:27])(=[O:26])=[O:25])[CH:19]=3)=[CH:14][CH:13]=2)[CH:11]=1)=O.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:46])=CC=1.C1(C)C=CC=CC=1.C1C=CC=CC=1>CCOCC>[F:1][C:2]([F:36])([F:35])[CH2:3][NH:4][C:5]([C:7]1[N:8]=[C:9]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[Cl:34])[N:10]([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([S:24]([CH3:27])(=[O:26])=[O:25])[CH:19]=3)=[CH:14][CH:13]=2)[CH:11]=1)=[S:46]

Participants

6

Reactant 4

HCID 241BenzeneHCID 1140TolueneHCID 87949Lawesson's reagentHCID 59251442HCID 59251442, compound

Product 1

HCID 59251258HCID 59251258, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a 25 mL round bottom flask attached with Vigreux column and magnetic stir bar was added 2-(2-Chloro-phenyl)-1-(3′-methanesulfonyl-biphenyl-4-yl)-1H-imidazole-4-carboxylic acid (2,2,2-trifluoro-ethyl)-amide (65 mg, 127 μmol), Lawesson's Reagent (230 mg, 570 μmol), and anhydrous toluene (6 mL). The reaction solution was allowed to stir at reflux 5 hrs prior to TLC analysis showing full transformation of starting material. The reaction solution was allowed to cool to room temperature prior to addition of a 1:1 mixture of benzene and Et2O. The resulting precipitate was removed by vacuum filtration through a Buchner funnel. The filtrate was concentrated on the Rotavapor and the crude residue was chromatographed through a 12 g SiO2 column using a mobile phase gradient of 100% Hx to 50% EtOAc to afford 55 mg (79% yield) of the title compound. 1H NMR (400 MHz, CDCl3) δ 9.21 (t, 1H), 8.11 (s, 1H), 8.04 (t, 1H), 7.85 (d, 1H), 7.75 (d, 1H), 7.59 (t, 1H), 7.53-7.46 (m, 4H), 7.34-7.311 (m, 3H), 7.18 (d, 2H), 4.56 (m, 2H), 3.02 (s, 3H); 19F NMR (400 MHz, CDCl3) δ −70.8 ppm; MS (ES): 550.3, 552.3 [M+H]+.

Workup

  1. customTo a 25 mL round bottom flask attached with Vigreux column and magnetic stir bar
  2. temperatureat reflux 5 hrs
  3. customThe resulting precipitate was removed by vacuum filtration through a Buchner funnel
  4. concentrationThe filtrate was concentrated on the Rotavapor
  5. customthe crude residue was chromatographed through a 12 g SiO2 column

Sources & evidence

ORD record
ord-fa976edff8804cfc882ca8a752d66522
Source dataset
uspto-grants-2015_04
Patent number
US09000022B2

Reaction notes

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