2-[bis(methylsulfanyl)methylene]-4,4-dibutyl-1,3(2H,4H)-naphthalenedione → 1,1-dibutyl-4-hydroxy-3-{7-[(methoxymethoxy)methyl]-1,1-dioxido-4H-thieno[2,3-e][1,2,4]thiadiazin-3-yl}-2(1H)-naphthalenone

HRID 494471Notes

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

Participants

Conditions

Temperature: 25 °C

Procedure

A mixture of the product of Example 5C (66 mg, 0.18 mmol) and the product of Example 10E (44 mg, 0.18 mmol) in toluene (10 mL) was stirred at reflux for 2 h, cooled to 25° C. and concentration in vacuo. The residue was chromatographed on silica gel, eluting with ethyl acetate in hexane to give the title compound (54 mg, 58%). 1H NMR (300 MHz, CDCl3): δ 16.44 (s, 1 H), 15.03, 14.86 (two s, 1 H), 8.27 (m, 1 H), 7.69 (m, 1 H), 7.49 (t, J=7.17 Hz, 1 H), 7.26 (m, 1 H), 7.08 (s, 1 H), 4.84 (s, 2 H), 4.80 (s, 2 H), 3.45 (s, 3 H), 2.33 (m, 2 H), 1.95 (m, 2 H), 1.13 (m, 4 H), 0.86 (m, 2 H), 0.69 (m, 6 H), 0.56 (m, 2 H).

Workup

temperatureat reflux for 2 h
concentrationconcentration in vacuo
customThe residue was chromatographed on silica gel
washeluting with ethyl acetate in hexane

Sources & evidence

ORD record: ord-ba1a21371e2040f78aaaa116ce34167d
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07538105B2

Reaction notes

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