Dimethyl Sulfoxide → HCID 11539559, compound

HRID 2069207Notes

Reaction equation

F[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[N+:12]([O-:14])=[O:13])[NH:8][C:7](=[O:15])[N:6]([NH:16][S:17]([CH3:20])(=[O:19])=[O:18])[C:5]2=[O:21].[Br:22][C:23]1[N:24]=[CH:25][NH:26][CH:27]=1.CS(C)=O.C(OCC)(=O)C>O>[Br:22][C:23]1[N:24]=[CH:25][N:26]([C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][C:11]=2[N+:12]([O-:14])=[O:13])[NH:8][C:7](=[O:15])[N:6]([NH:16][S:17]([CH3:20])(=[O:19])=[O:18])[C:5]3=[O:21])[CH:27]=1

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 20 mg (0.062 mmol) of N-(6-fluoro-7-nitro-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl)-methanesulfonamide, 56 mg (0.372 mmol) of 4-bromo-1H-imidazole and 0.1 ml of DMSO is heated to 120° C. for 16 hours. After cooling to room temperature, the reaction mixture is distributed between ethyl acetate and water, the organic phase is separated, washed with water and brine, dried over sodium sulfate, filtered and evaporated. The residue is chromatographed on silica gel using dichloro-methane-methanol (95:5) and the fractions containing the desired product are combined and evaporated yielding 6 mg (21%) of the title compound. MS (ES−): m/e=445 (M−).

Workup

temperatureAfter cooling to room temperature
customthe organic phase is separated
washwashed with water and brine
dry with materialdried over sodium sulfate
filtrationfiltered
customevaporated
customThe residue is chromatographed on silica gel
additionthe fractions containing the desired product
customevaporated

Sources & evidence

ORD record: ord-558dd220fe12477c9de3428e8f0dd92a
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08299085B2

Reaction notes

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