Dimethyl Sulfoxide → HCID 11539494, compound

HRID 2069208Notes

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].[C:22]1([C:28]2[N:29]=[CH:30][NH:31][CH:32]=2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.CS(C)=O.C(OCC)(=O)C>O>[N+:12]([C:11]1[CH:10]=[C:9]2[C:4]([C:5](=[O:21])[N:6]([NH:16][S:17]([CH3:20])(=[O:19])=[O:18])[C:7](=[O:15])[NH:8]2)=[CH:3][C:2]=1[N:31]1[CH:32]=[C:28]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:29]=[CH:30]1)([O-:14])=[O:13]

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 50 mg (0.156 mmol) of N-(6-fluoro-7-nitro-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl)-methanesulfonamide, 139 mg (0.936 mmol) of 4-phenyl-1H-imidazole and 0.25 ml of DMSO is heated to 120° C. for 3.5 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 tetrahydrofuran-hexane (80:20) and the fractions containing the desired product are combined and evaporated giving 53 mg (77%) of the title compound. MS (ES−): m/e=441 (M−1−).

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-110f7cb3996749f88e8fdc817dccb506
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08299085B2

Reaction notes

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