4-(3-chloro-1,4-dioxo-1,4-dihydro-naphthalen-2-ylamino)-N-(3-methoxy-phenyl)-benzenesulfonamide → N-[4-hydroxy-3-(1H-1,2,4-triazol-3-ylsulfanyl)naphthalen-1-yl]thiophene-2-sulfonamide

HRID 1186668Notes

Reaction equation

HRID 1186668 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([NH:12][S:13]([C:16]2[S:17][CH:18]=[CH:19][CH:20]=2)(=[O:15])=[O:14])=[CH:4][C:3]=1[S:21][C:22]1[N:26]([CH3:27])N=[N:24][N:23]=1.ClC1C(=O)C2C(=CC=CC=2)C(=O)C=1NC1C=CC(S(NC2C=CC=C(OC)C=2)(=O)=O)=CC=1>>[NH:23]1[C:22]([S:21][C:3]2[CH:4]=[C:5]([NH:12][S:13]([C:16]3[S:17][CH:18]=[CH:19][CH:20]=3)(=[O:15])=[O:14])[C:6]3[C:11]([C:2]=2[OH:1])=[CH:10][CH:9]=[CH:8][CH:7]=3)=[N:26][CH:27]=[N:24]1

Participants

3

Reactant 2

HCID 446088204-(3-chloro-1,4-dioxo-1,4-dihydro-naphthalen-2-ylamino)-N-(3-methoxy-phenyl)-benzenesulfonamideHCID 135895396N-(4-hydroxy-3-(1-methyl-1H-tetrazol-5-ylthio)naphthalen-1-yl)thiophene-2-sulfonamide

Product 1

HCID 2133817N-[4-hydroxy-3-(1H-1,2,4-triazol-3-ylsulfanyl)naphthalen-1-yl]thiophene-2-sulfonamide

Procedure

5.2.48 N-(3-(1H-1,2,4-triazol-5-ylthio)-4-hydroxynaphthalen-1-yl)thiophene-2-sulfonamide (14e) was prepared according to the procedure for 14d except using (E)-N-(3-(1H-1,2,4-triazol-5-ylthio)-4-oxonaphthalen-1(4H)-ylidene)thiophene-2-sulfonamide (13e), which afforded the title compound 20 mg (100%) as a white solid, m.p.: 180° C. (dec.).

Sources & evidence

ORD record
ord-e8aa876b948344ceae5bc3e83bc59884
Source dataset
uspto-grants-2014_03
Patent number
US08673910B2

Reaction notes

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