Benzene → HCID 59632205, compound

HRID 2369107Notes

Reaction equation

HRID 2369107 reaction equation
[CH2:1]([NH:3][C:4]([C:6]1[CH:10]=[C:9]([C:11]2[S:12][C:13]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([S:22]([CH3:25])(=[O:24])=[O:23])[CH:17]=3)=[CH:14][CH:15]=2)[N:8]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[Cl:32])[N:7]=1)=O)[CH3:2].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:42])=CC=1.C1(C)C=CC=CC=1.C1C=CC=CC=1>CCOCC>[CH2:1]([NH:3][C:4]([C:6]1[CH:10]=[C:9]([C:11]2[S:12][C:13]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([S:22]([CH3:25])(=[O:24])=[O:23])[CH:17]=3)=[CH:14][CH:15]=2)[N:8]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[Cl:32])[N:7]=1)=[S:42])[CH3:2]

Participants

6

Reactant 4

HCID 241BenzeneHCID 1140TolueneHCID 87949Lawesson's reagentHCID 59633427HCID 59633427, compound

Product 1

HCID 59632205HCID 59632205, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a dry, N2 purged 50 mL round bottom flask attached with condenser was added 1-(2-Chloro-phenyl)-5-[5-(3-methanesulfonyl-phenyl)-thiophen-2-yl]-1H-pyrazole-3-carboxylic acid ethylamide (100 mg, 206 μmol), Lawesson's reagent (200 mg, 494 μmol), and anhydrous toluene (8 mL). The reaction solution was allowed to stir at reflux for 14 hrs. 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 39 mg (38% yield) of the title compound. 1H NMR (400 MHz, CDCl3) δ 8.68 (br s, 1H), 8.02 (s, 1H), 7.83 (d, 1H), 7.72 (d, 1H), 7.48-7.70 (m, 5H), 7.42 (s, 1H), 7.22 (d, 1H), 6.83 (d, 1H), 3.87 (m, 2H), 3.07 (s, 3H), 1.36 (t, 3H). MS (ES) 502.3, 504.3 [M+H]+.

Workup

  1. customTo a dry, N2 purged 50 mL round bottom flask
  2. customattached with condenser
  3. temperatureat reflux for 14 hrs
  4. customThe resulting precipitate was removed by vacuum filtration through a Buchner funnel
  5. concentrationThe filtrate was concentrated on the Rotavapor
  6. customthe crude residue was chromatographed through a 12 g SiO2 column

Sources & evidence

ORD record
ord-b9732f709f7b4d4cb7649db2410f349c
Source dataset
uspto-grants-2014_04
Patent number
US08703805B2

Reaction notes

Loading…