4-Hydroxybenzoic Acid → HCID 58453271, compound

HRID 2284383Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([N:9]([CH2:19][C:20]2[NH:21][NH:22][C:23](=[O:25])[CH:24]=2)S(C2C=CC=CC=2)(=O)=O)[CH:5]=[C:6]([Cl:8])[CH:7]=1.OC1C=CC(C(O)=O)=CC=1.Br>CC(O)=O>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][CH2:19][C:20]2[NH:21][NH:22][C:23](=[O:25])[CH:24]=2)[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

Conditions

Temperature: 100 °C

Procedure

N-(3,5-dichlorophenyl)-N-((5-oxo-2,5-dihydro-1H-pyrazol-3-yl)methyl)benzenesulfonamide (398 mg, 1 mmol) and 4-hydroxybenzoic acid (800 mg, 5.8 mmol, 200% weight) were added to a solution of HBr (48% in H2O, 4 mL) and AcOH (4 mL). After the resulting suspension was stirred at 100° C. for 2 h, the reaction mixture was partitioned between 1N HCl (10 mL) and ethyl acetate (30 mL×2). The collected organic layers were combined, dried over Na2SO4, filtered, and concentrated. The residue was subjected to column chromatography eluting with a mixture of MeOH and dichloromethane (5% MeOH) to afford 2 (142 mg, 55% yield) as a white solid. 1H NMR (DMSO-d6, 500 MHz): δ=6.65 (t, J=5.5 Hz, 1H), 6.61 (s, 1H), 6.59, (s, 2H), 5.35 (s, 1H), 4.10 (d, J=5.0 Hz, 2H); 13C NMR (DMSO-d6, 125 MHz): δ=150.7, 134.3X2, 114.6, 110.4X2 ppm; MS (ESI): m/z 280.0 [M+Na]+; CHN calculated for C10H9Cl2N3O: C, 46.53; H, 3.51; N, 16.28. found: C, 46.44; H, 3.61; N, 16.36.

Workup

customthe reaction mixture was partitioned between 1N HCl (10 mL) and ethyl acetate (30 mL×2)
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated
washeluting with a mixture of MeOH and dichloromethane (5% MeOH)

Sources & evidence

ORD record: ord-bc28322bd2574676bae02936a02767ba
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09145424B2

Reaction notes

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