Sulfanilamide → HCID 59807751, compound

HRID 383732Notes

Reaction equation

[CH3:1][C:2]1[N:3]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][C:12]=2[C:18]([F:21])([F:20])[F:19])[C:4]([CH3:10])=[CH:5][C:6]=1[C:7](Cl)=[O:8].[S:22]([NH2:32])(=[O:31])([C:24]1[CH:29]=[CH:28][C:27]([NH2:30])=[CH:26][CH:25]=1)=[O:23].C(N(C(C)C)CC)(C)C>C1COCC1>[S:22]([C:24]1[CH:25]=[CH:26][C:27]([NH:30][C:7]([C:6]2[CH:5]=[C:4]([CH3:10])[N:3]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][C:12]=3[C:18]([F:21])([F:20])[F:19])[C:2]=2[CH3:1])=[O:8])=[CH:28][CH:29]=1)(=[O:23])(=[O:31])[NH2:32]

Participants

Conditions

Temperature: 80 °C

Procedure

Into an oven-dried 1 dram vial was added 2,5-dimethyl-1-[4-fluoro-2-(trifluoromethyl)phenyl]-1H-pyrrole-3-carboxylic acid chloride (106 mg, 332 μmol), sulfanilamide (62.0 mg, 360 μmol), anhyd THF (2.0 mL) and diisopropylethylamine (50 μL). The vial was sealed and heated at 80° C. overnight. The resulting residue was purified by flash chromatography (SiO2), eluting with EtOAc/Hex (30:70 to 60:40) to afford the title compound as an off-white solid (99 mg, 66%); 1H NMR (CDCl3): δ 8.85 (s, 1H), 7.88 (d, J=7 Hz, 2H), 7.84 (d, J=7 Hz, 2H), 7.58 (dd, J=8, 3 Hz, 1H), 7.46 (m, 1H), 7.31 (dd, J=5, 8 Hz, 1H), 6.46 (s, 1H), 6.19 (s, 2H), 2.25 (s, 3H), 1.94 (s, 3H); MS (ESI) m/z 456 [M+H]+. D. In a manner similar to that described in Examples 1A-1C, but replacing 4-fluoro-2-(trifluoromethyl)aniline with 2-(trifluoromethyl)aniline, the following compound was prepared:

Workup

customThe vial was sealed
customThe resulting residue was purified by flash chromatography (SiO2)
washeluting with EtOAc/Hex (30:70 to 60:40)

Sources & evidence

ORD record: ord-bb7f604f09e84246801365d34e643120
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08367667B2

Reaction notes

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