Benzoic acid, 3-(chlorosulfonyl)- → 3-{[Ethylamino-(4-ethyl-4,5-dihydro-pyrazol-1-yl)-methylene]-sulfamoyl}-benzoic acid

HRID 1044709Notes

Reaction equation

HRID 1044709 reaction equation
[CH2:1]([CH:3]1[CH2:7][N:6]([C:8]([NH:10][CH2:11][CH3:12])=[NH:9])[N:5]=[CH:4]1)[CH3:2].CCN(C(C)C)C(C)C.Cl[S:23]([C:26]1[CH:27]=[C:28]([CH:32]=[CH:33][CH:34]=1)[C:29]([OH:31])=[O:30])(=[O:25])=[O:24]>C(Cl)Cl>[CH2:11]([NH:10][C:8](=[N:9][S:23]([C:26]1[CH:27]=[C:28]([CH:32]=[CH:33][CH:34]=1)[C:29]([OH:31])=[O:30])(=[O:25])=[O:24])[N:6]1[CH2:7][CH:3]([CH2:1][CH3:2])[CH:4]=[N:5]1)[CH3:12]

Participants

5

Reactant 3

HCID 77641Benzoic acid, 3-(chlorosulfonyl)-HCID 81531DiisopropylethylamineHCID 178464602HCID 178464602, compound

Product 1

HCID 1784646493-{[Ethylamino-(4-ethyl-4,5-dihydro-pyrazol-1-yl)-methylene]-sulfamoyl}-benzoic acidYield 4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under N2 atmosphere, 1.0 g 4,N-diethyl-4,5-dihydro-pyrazole-1-carboxamidine was dissolved in 15 mL dry DCM, and 1.14 mL DiPEA and 1.31 g of 3-(chlorosulfonyl)benzoic acid were added. The mixture was stirred overnight at room temperature and evaporated to dryness. The residue was purified by flash chromatography (first column with DCM/MeOH/acetic acid 84:15:1; second column with DCM/MeOH/NH4OH 84:15:1) to yield 0.08 g (4%) of an off-white powder. 1H NMR (400 MHz, CDCl3) δ 0.90 (t, J=7.4 Hz, 3H), 1.14 (t, J=7.2 Hz, 3H), 1.38-1.62 (m, 2H), 3.02-3.18 (m, 1H), 3.27-3.62 (m, 3H), 3.89-4.17 (m, 1H), 6.94 (s, 1H), 7.26 (t, J=7.8 Hz, 1H), 7.89 (d, J=7.8 Hz, 1H), 8.05 (d, J=7.8 Hz, 1H), 8.49 (s, 1H).

Workup

  1. customevaporated to dryness
  2. customThe residue was purified by flash chromatography (first column with DCM/MeOH/acetic acid 84:15:1; second column with DCM/MeOH/NH4OH 84:15:1)

Sources & evidence

ORD record
ord-8fef4e47eab44fd793a55a31c7f223ed
Source dataset
uspto-grants-2013_10
Patent number
US08563723B2

Reaction notes

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