Reaction equation
Cl[Sb-](Cl)(Cl)(Cl)(Cl)Cl.ClOC(N(C)C)=[N+](C)C.[Cl:17][C:18]1[CH:19]=[N:20][CH:21]=[C:22]([Cl:36])[C:23]=1[S:24][C:25]1[S:29][C:28]([C:30]([OH:32])=O)=[CH:27][C:26]=1[N+:33]([O-:35])=[O:34].[CH:37]([NH2:40])([CH3:39])[CH3:38].C(N(CC)CC)C>ClCCl>[Cl:36][C:22]1[CH:21]=[N:20][CH:19]=[C:18]([Cl:17])[C:23]=1[S:24][C:25]1[S:29][C:28]([C:30]([NH:40][CH:37]([CH3:39])[CH3:38])=[O:32])=[CH:27][C:26]=1[N+:33]([O-:35])=[O:34]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
Chloro-1,1,3,3-tetramethyluronium hexachloroantimonate (47 mg, 0.1 mmol) was added to a suspension of 5-[(3,5-dichloro-4-pyridyl)sulfanyl]-4-nitro-thiophene-2-carboxylic acid (39 mg, 0.11 mmol) in dichloromethane (1 mL) and the mixture was stirred at ambient temperature for 10 min. A solution of isopropylamine (9 mg, 0.12 mmol) and triethylamine (12 mg, 0.12 mmol) in dichloromethane (0.5 mL) was added to the above mixture and was stirred at ambient temperature for over night. After passing through a ISOLUTE™ PE-AX cartridge to remove excess amines, the resulting mixture was concentrated and the residue was purified by reverse-phase HPLC to afford the title product as a white solid (25 mg, 49% yield). 1H NMR (300 MHz, d6-DMSO) δ: 9.0 (2H, s), 8.65 (1H, d), 8.50 (1H, s), 4.0 (1H, m), 1.25 (6H, d). MS m/z: 391.70, 393.80 [M+H]+.
Workup
- stirringwas stirred at ambient temperature for over night
- customto remove excess amines
- concentrationthe resulting mixture was concentrated
- customthe residue was purified by reverse-phase HPLC
Sources & evidence
- ORD record
- ord-0c7ac7762bf64e229dcb91c43cb02e4a
- Source dataset
- uspto-grants-2014_03
- Patent number
- US08680139B2
Linked notes
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