2-Aminobenzenesulfonamide → 3-(1,1-Dioxido-4h-1,2,4-benzothiadiazin-3-yl)-6-fluoro-4-hydroxy-1,1-dipropylnaphthalen-2(1h)-one

HRID 494478Notes

Reaction equation

HRID 494478 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][CH:54]=[CH:53][C:52]=1[S:57]([NH2:60])(=[O:59])=[O:58].NC1C=CC(OCC2C=CC=CC=2)=CC=1S(N)(=O)=O>>[O:58]=[S:57]1(=[O:59])[C:52]2[CH:53]=[CH:54][CH:55]=[CH:56][C:51]=2[NH:50][C:3]([C:4]2[C:13](=[O:14])[C:12]([CH2:18][CH2:19][CH3:20])([CH2:15][CH2:16][CH3:17])[C:11]3[C:6]([C:5]=2[OH:22])=[CH:7][C:8]([F:21])=[CH:9][CH:10]=3)=[N:60]1

Participants

5

Reactant 4

HCID 728942-AminobenzenesulfonamideHCID 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 670639862-Amino-5-(benzyloxy)benzenesulfonamide

Product 1

HCID 1363375473-(1,1-Dioxido-4h-1,2,4-benzothiadiazin-3-yl)-6-fluoro-4-hydroxy-1,1-dipropylnaphthalen-2(1h)-one

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 also substituting 2-aminobenzenesulfonamide for the compound of Example 2D. 1H NMR (300 MHz, DMSO-d6): δ 0.58 (m, 2 H) 0.67 (m, 6 H) 0.93 (m, 2 H) 2.01 (m, 2 H) 2.17 (m, 2 H) 7.72 (m, 7 H) 13.48 (s, 1-H).

Sources & evidence

ORD record
ord-e193b61643e940a58bf1f9e4fa7d4f8b
Source dataset
uspto-grants-2009_05
Patent number
US07538105B2

Reaction notes

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