2-[Bis(methylthio)methylene]-4-butyl-4-methylnaphthalene-1,3(2h,4h)-dione → Tert-butyl 3-(4-butyl-1-hydroxy-4-methyl-3-oxo-3,4-dihydronaphthalen-2-yl)-1,1-dioxido-4h-1,2,4-benzothiadiazin-7-ylcarbamate

HRID 494527Notes

Reaction equation

CS[C:3](SC)=[C:4]1[C:13](=[O:14])[C:12]([CH2:16][CH2:17][CH2:18][CH3:19])([CH3:15])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]1=[O:20].[C:23]([O:27][C:28](=[O:41])[NH:29][C:30]1[CH:35]=[CH:34][C:33]([NH2:36])=[C:32]([S:37](=[O:40])(=[O:39])[NH2:38])[CH:31]=1)([CH3:26])([CH3:25])[CH3:24]>C1(C)C=CC=CC=1>[CH2:16]([C:12]1([CH3:15])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([OH:20])=[C:4]([C:3]2[NH:36][C:33]3[CH:34]=[CH:35][C:30]([NH:29][C:28](=[O:41])[O:27][C:23]([CH3:26])([CH3:24])[CH3:25])=[CH:31][C:32]=3[S:37](=[O:39])(=[O:40])[N:38]=2)[C:13]1=[O:14])[CH2:17][CH2:18][CH3:19]

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of Example 27F (0.296 g, 0.885 mmol) and (4-amino-3-sulfamoyl-phenyl)-carbamic acid tert-butyl ester (0.280 g, 0.973 mmol) in toluene (40 mL) was refluxed for 6 hours. The solution was cooled to 25° C. and concentrated in vacuo. The residue was chromatographed on silica gel eluting with hexane followed by 20% and 30% ethyl acetate in hexane to give the title compound (0.430 g, 92%). 1H NMR (300 MHz, DMSO-d6): δ ppm 0.53 (m, 1 H) 0.69 (m, 3 H) 0.87 (m, 1 H) 1.08 (m, 2 H) 1.46 (m, 9 H) 1.55 (m, 3 H) 2.01 (m, 1 H) 2.20 (m, 1 H) 7.60 (m, 5 H) 8.13 (m, 2 H) 9.83 (m, 1 H) 13.93 (m, 1 H). MS (ESI−) m/z 524 (M−H)−.

Workup

concentrationconcentrated in vacuo
customThe residue was chromatographed on silica gel eluting with hexane

Sources & evidence

ORD record: ord-95db5661ea7d472181c635ff6a7353e9
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07538105B2

Reaction notes

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