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 494481Notes

Reaction equation

HRID 494481 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-0fecbf78c43348eaa1bce668290cdcfa
Source dataset
uspto-grants-2009_05
Patent number
US07538105B2

Reaction notes

Loading…