3-Methylthiopropionate → 4-tert-butyl-N-{4-chloro-5-fluoro-2-[N'-(3-methylsulfanyl-propionyl)-hydrazinocarbonyl]-phenyl}-benzenesulfonamide

HRID 448117Notes

Reaction equation

HRID 448117 reaction equation
[CH3:1][S:2][CH2:3][CH2:4][C:5]([OH:7])=O.C(Cl)(=O)C(Cl)=O.[C:14]([C:18]1[CH:23]=[CH:22][C:21]([S:24]([NH:27][C:28]2[CH:33]=[C:32]([F:34])[C:31]([Cl:35])=[CH:30][C:29]=2[C:36]([NH:38][NH2:39])=[O:37])(=[O:26])=[O:25])=[CH:20][CH:19]=1)([CH3:17])([CH3:16])[CH3:15].CCN(CC)CC>C(Cl)Cl.CN(C=O)C>[C:14]([C:18]1[CH:23]=[CH:22][C:21]([S:24]([NH:27][C:28]2[CH:33]=[C:32]([F:34])[C:31]([Cl:35])=[CH:30][C:29]=2[C:36]([NH:38][NH:39][C:5](=[O:7])[CH2:4][CH2:3][S:2][CH3:1])=[O:37])(=[O:25])=[O:26])=[CH:20][CH:19]=1)([CH3:17])([CH3:15])[CH3:16]

Participants

7

Reactant 4

HCID 5633-MethylthiopropionateHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 593029664-tert-butyl-N-(4-chloro-5-fluoro-2-hydrazinocarbonyl-phenyl)-benzenesulfonamide

Product 1

HCID 593030414-tert-butyl-N-{4-chloro-5-fluoro-2-[N'-(3-methylsulfanyl-propionyl)-hydrazinocarbonyl]-phenyl}-benzenesulfonamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 3-methylsulfanyl-propionic acid (120 mg, 1.0 mmol) under an inert atmosphere in 6 mL of anhydrous DCM and DMF (200 μL) was added oxalyl chloride (89 μL, 1.0 mmol). The resultant solution was stirred at room temperature overnight and then added to a solution of 4-tert-butyl-N-(4-chloro-5-fluoro-2-hydrazinocarbonyl-phenyl)-benzenesulfonamide (400 mg, 1.0 mmol) and Et3N (0.35 mL, 2.5 mmol) at 0° C. The resultant solution was stirred at room temperature for 4 hours and the solvent was removed in vacuo. The residue was purified via automated silica gel chromatography to afford 4-tert-butyl-N-{4-chloro-5-fluoro-2-[N′-(3-methylsulfanyl-propionyl)-hydrazinocarbonyl]-phenyl}-benzenesulfonamide as an oil: MS (ES) M+H expected 502.1, found 502.0.

Workup

  1. customthe solvent was removed in vacuo
  2. customThe residue was purified

Sources & evidence

ORD record
ord-bde5ac37ac86412b9ad8f533754c68b2
Source dataset
uspto-grants-2013_07
Patent number
US08481579B2

Reaction notes

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