2-[bis(methylsulfanyl)methylene]-4,4-dibutyl-1,3(2H,4H)-naphthalenedione → Tert-butyl 3-(7-fluoro-1-hydroxy-3-oxo-4,4-dipropyl-3,4-dihydronaphthalen-2-yl)-1,1-dioxido-4h-1,2,4-benzothiadiazin-7-ylcarbamate

HRID 2224802Notes

Reaction equation

HRID 2224802 reaction equation
CS[C:3](SC)=[C:4]1[C:13](=[O:14])[C:12]([CH2:18][CH2:19][CH3:20])([CH2:15][CH2:16][CH3:17])[C:11]2[C:6](=[CH:7][C:8]([F:21])=[CH:9][CH:10]=2)[C:5]1=[O:22].CSC(SC)=C1C(=O)C(CCCC)(CCCC)C2C(=CC=CC=2)C1=O.[NH2:50][C:51]1[CH:56]=[CH:55][C:54]([NH:57][C:58](=[O:64])[O:59][C:60]([CH3:63])([CH3:62])[CH3:61])=[CH:53][C:52]=1[S:65]([NH2:68])(=[O:67])=[O:66].NC1C=CC(OCC2C=CC=CC=2)=CC=1S(N)(=O)=O>>[F:21][C:8]1[CH:7]=[C:6]2[C:11]([C:12]([CH2:15][CH2:16][CH3:17])([CH2:18][CH2:19][CH3:20])[C:13](=[O:14])[C:4]([C:3]3[NH:50][C:51]4[CH:56]=[CH:55][C:54]([NH:57][C:58](=[O:64])[O:59][C:60]([CH3:62])([CH3:63])[CH3:61])=[CH:53][C:52]=4[S:65](=[O:66])(=[O:67])[N:68]=3)=[C:5]2[OH:22])=[CH:10][CH:9]=1

Participants

5

Reactant 4

HCID 112111042-[bis(methylsulfanyl)methylene]-4,4-dibutyl-1,3(2H,4H)-naphthalenedioneHCID 114854142-[Bis(methylthio)methylene]-7-fluoro-4,4-dipropylnaphthalene-1,3(2h,4h)-dioneHCID 59805694HCID 59805694, compoundHCID 670639862-Amino-5-(benzyloxy)benzenesulfonamide

Product 1

HCID 136384912Tert-butyl 3-(7-fluoro-1-hydroxy-3-oxo-4,4-dipropyl-3,4-dihydronaphthalen-2-yl)-1,1-dioxido-4h-1,2,4-benzothiadiazin-7-ylcarbamate

Procedure

The title compound was prepared according to the procedure of Example 5D, substituting the compound of Example 14H for the compound of Example 5C, and the compound of Example 17A for the compound of Example 2D. 1H NMR (300 MHz, DMSO-d6): δ 0.62 (m, 8 H) 0.91 (m, 2 H) 1.47 (d, J=17.28 Hz, 9 H) 1.93 (m, 2 H) 2.10 (m, 2 H) 7.63 (m, 5 H) 8.03 (s, 1 H) 9.77 (s, 1 H) 14.21 (s, 1 H).

Sources & evidence

ORD record
ord-4e86dee7931344f9bf94aa455164a549
Source dataset
uspto-grants-2008_05
Patent number
US07378414B2

Reaction notes

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