(Methoxycarbonylsulfamoyl)triethylammonium hydroxide → HCID 58958573, compound

HRID 915600Notes

Reaction equation

HRID 915600 reaction equation
[OH:1]/[N:2]=[C:3](\[NH:5][C:6](=O)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[NH:13][C:14]1[N:18]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:17]=[C:16]([CH3:25])[CH:15]=1)/[CH3:4].[OH-].[CH3:28][O:29]C(NS([N+](CC)(CC)CC)(=O)=O)=O>C1COCC1>[CH3:28][O:29][C:11]1[CH:10]=[CH:9][C:8]([NH:13][C:14]2[N:18]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[N:17]=[C:16]([CH3:25])[CH:15]=2)=[C:7]([C:6]2[O:1][N:2]=[C:3]([CH3:4])[N:5]=2)[CH:12]=1

Participants

4

Reactant 2

HCID 11032497(Methoxycarbonylsulfamoyl)triethylammonium hydroxideHCID 136410149HCID 136410149, compound

Product 1

HCID 58958573HCID 58958573, compoundYield 4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the crude N-[(1Z)-N-hydroxyethanimidoyl]-2-[(3-methyl-1-phenyl-1H-pyrazol-5-yl)amino]benzamide (257 mg, 0.41 mmol) in THF (3 mL) was added (methoxycarbonylsulfamoyl)triethylammonium hydroxide (Burgess reagent) (145 mg, 0.61 mmol). The flask was flushed with argon and refluxed for 3 h under argon. The reaction mixture was the cooled to rt, filtered through a small plug of silica gel, and the plug was eluted with EtOAc. The filtrate was concentrated under reduced pressure, and the residue purified by preparative TLC on silica gel using EtOAc/Hex (1:2, v/v) to give the title product as a solid (5.5 mg, 4% overall). 1H NMR (400 MHz, CD3CN). δ 2.30 (s, 3H), 2.32 (s, 3H), 3.82 (s, 3H), 6.16 (s, 1H), 7.09 (dd, 1H), 7.21 (d, 1H), 7.38-7.42 (m, 1H), 7.42-7.50 (m, 3H), 7.50-7.58 (m, 2H), 9.46 (br, s, 1H). ES-MS m/z 362.2 (MH+); HPLC RT (min) 3.28.

Workup

  1. customThe flask was flushed with argon
  2. temperaturerefluxed for 3 h under argon
  3. filtrationfiltered through a small plug of silica gel
  4. washthe plug was eluted with EtOAc
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customthe residue purified by preparative TLC on silica gel

Sources & evidence

ORD record
ord-502a8e5879b44dca82952c0d31aba585
Source dataset
uspto-grants-2007_09
Patent number
US07265144B2

Reaction notes

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