Ammonia → HCID 57750898, compound

HRID 2283297Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:10]=[C:11]([S:15]([NH:18][C:19]3[CH:27]=[CH:26][C:22]([C:23](O)=[O:24])=[CH:21][C:20]=3[S:28](=[O:31])(=[O:30])[NH2:29])(=[O:17])=[O:16])[CH:12]=[CH:13][CH:14]=2)[CH:5]=[CH:6][C:7]=1[Cl:8].C(N1C=CN=C1)([N:34]1C=CN=C1)=O.N.Cl>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:10]=[C:11]([S:15]([NH:18][C:19]3[CH:27]=[CH:26][C:22]([C:23]([NH2:34])=[O:24])=[CH:21][C:20]=3[S:28](=[O:31])(=[O:30])[NH2:29])(=[O:17])=[O:16])[CH:12]=[CH:13][CH:14]=2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 4-[[3-(3,4-dichlorophenyl)phenyl]sulfonylamino]-3-sulfamoylbenzoic acid (0.20 g, 0.39 mmol) in DMF (5 mL) was added carbonyldiimidazole (0.06 g, 0.39 mmol). The reaction mixture was heated at 80° C. for 2 h, then aqueous ammonia solution (30%, 2 mL) was added and the resulting solution was stirred at RT for 2 h. The pH of the reaction mixture was then adjusted to pH 5 using 6N HCl and the resulting white precipitate was collected by filtration. The crude product was purified by preparative HPLC to afford the title compound (13 mg, 7%).

Workup

filtrationthe resulting white precipitate was collected by filtration
customThe crude product was purified by preparative HPLC

Sources & evidence

ORD record: ord-264afc56fe6844a39ddc18c648f23ca9
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09145380B2

Reaction notes

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