2-[bis(methylsulfanyl)methylene]-4,4-dibutyl-1,3(2H,4H)-naphthalenedione → 3-[7-(benzyloxy)-1,1-dioxido-4H-1,2,4-benzothiadiazin-3-yl]-1,1-dibutyl-4-hydroxy-2(1H)-naphthalenone

HRID 494456Notes

Reaction equation

CS[C:3](SC)=[C:4]1[C:13](=[O:14])[C:12]([CH2:19][CH2:20][CH2:21][CH3:22])([CH2:15][CH2:16][CH2:17][CH3:18])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]1=[O:23].[NH2:26][C:27]1[CH:32]=[CH:31][C:30]([O:33][CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)=[CH:29][C:28]=1[S:41]([NH2:44])(=[O:43])=[O:42]>C1(C)C=CC=CC=1>[CH2:34]([O:33][C:30]1[CH:31]=[CH:32][C:27]2[NH:26][C:3]([C:4]3[C:13](=[O:14])[C:12]([CH2:19][CH2:20][CH2:21][CH3:22])([CH2:15][CH2:16][CH2:17][CH3:18])[C:11]4[C:6]([C:5]=3[OH:23])=[CH:7][CH:8]=[CH:9][CH:10]=4)=[N:44][S:41](=[O:42])(=[O:43])[C:28]=2[CH:29]=1)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of the product of Example 5C (52 mg, 0.14 mmol) and the product of Example 2D (38 mg, 0.14 mmol) in toluene (12 mL) was stirred at reflux for 6 hours, cooled to 25° C. and concentrated in vacuo. The residue was triturated with ether-hexane and collected by filtration to give the title compound (65 mg, 84%). 1H NMR (300 MHz, CDCl3): δ 16.66 (m, 1 H), 14.33 (s, 1 H), 8.27 (d, J=8.09 Hz, 1 H), 7.66 (m, 1 H), 7.38 (m, 10 H), 5.14 (s, 2 H), 2.35 (m, 2 H), 1.96 (m, 2 H), 1.12 (m, 4 H), 0.89 (m, 2 H), 0.70 (m, 6 H), 0.55 (m, 2H).

Workup

temperatureat reflux for 6 hours
concentrationconcentrated in vacuo
customThe residue was triturated with ether-hexane
filtrationcollected by filtration

Sources & evidence

ORD record: ord-edc54fdd890644f898f0ba1d5da270f2
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07538105B2

Reaction notes

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