1-Benzyl-3-(bis-methylsulfanyl-methylene)-1H-quinoline-2,4-dione → 1-benzyl-3-(7-benzyl-1,1-dioxido-4,7-dihydroimidazo[4,5-e][1,2,4]thiadiazin-3-yl)-4-hydroxyquinolin-2(1H)-one

HRID 601301Notes

Reaction equation

[NH2:1][C:2]1[N:3]=[CH:4][N:5]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:6]=1[S:7]([NH2:10])(=[O:9])=[O:8].[CH2:18]([N:25]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:28](=[O:35])[C:27](=[C:36](SC)SC)[C:26]1=[O:41])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C1(C)C=CC=CC=1>[CH2:18]([N:25]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:28]([OH:35])=[C:27]([C:36]2[NH:1][C:2]3[N:3]=[CH:4][N:5]([CH2:11][C:12]4[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=4)[C:6]=3[S:7](=[O:9])(=[O:8])[N:10]=2)[C:26]1=[O:41])[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

Conditions

Temperature: 25 °C

Procedure

The product of Example 312F (152 mg, 0.602 mmol) was reacted with the product of Example 309B (214 mg, 0.602 mmol) in toluene (8 mL) at 100° C. for 3 hours. The reaction was allowed to cool to 25° C. and diluted with hexanes. The resulting precipitate was collected by filtration. The residue was chromatographed on silica gel, eluting with gradient of 0-2% methanol in dichloromethane to give the title compound (155 mg, 50%). MS (ESI+) m/z 512 (M+H)+. 1H NMR (300 MHz, DMSO-d6) δ ppm 5.42 (s, 2H), 5.63 (s, 2H), 7.22-7.44 (m, 11H), 7.53-7.56 (m, 1H), 7.74-7.79 (m, 1H), 8.20-8.23 (dd, J=8.1, 1.5 Hz, 1H), 8.32 (s, 1H).

Workup

filtrationThe resulting precipitate was collected by filtration
customThe residue was chromatographed on silica gel
washeluting with gradient of 0-2% methanol in dichloromethane

Sources & evidence

ORD record: ord-7780184c8c7a4ece8afe30c30f72c07e
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07902203B2

Reaction notes

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