4-(3-chloro-1,4-dioxo-1,4-dihydro-naphthalen-2-ylamino)-2-methoxy-N-m-tolyl-benzenesulfonamide → N-(4-hydroxy-3-(2-hydroxyethylthio)naphthalen-1-yl)thiophene-2-sulfonamide

HRID 1186671Notes

Reaction equation

HRID 1186671 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]1N(C)N=NN=1.ClC1[C:38](=[O:39])C2C(=CC=CC=2)C(=O)C=1NC1C=CC(S(NC2C=C(C)C=CC=2)(=O)=O)=C(OC)C=1>>[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][CH2:22][CH2:38][OH:39]

Participants

3

Reactant 2

HCID 673292814-(3-chloro-1,4-dioxo-1,4-dihydro-naphthalen-2-ylamino)-2-methoxy-N-m-tolyl-benzenesulfonamideHCID 135895396N-(4-hydroxy-3-(1-methyl-1H-tetrazol-5-ylthio)naphthalen-1-yl)thiophene-2-sulfonamide

Product 1

HCID 46908187N-(4-hydroxy-3-(2-hydroxyethylthio)naphthalen-1-yl)thiophene-2-sulfonamide

Procedure

5.2.53 N-(4-hydroxy-3-(2-hydroxyethylthio)naphthalen-1-yl)thiophene-2-sulfonamide (14k) was prepared according to the procedure for 14d except using N-(3-(2-hydroxyethylthio)-4-oxonaphthalen-1(4H)-ylidene)thiophene-2-sulfonamide (13k), which, after purification via flash chromatography (Hex/EtOAc), afforded the title compound 20.3 mg (53.1%) as a grey solid, m.p.: ° C.

Workup

  1. customafter purification via flash chromatography (Hex/EtOAc)

Sources & evidence

ORD record
ord-8bbcc088e67641f5acf4e74e47355862
Source dataset
uspto-grants-2014_03
Patent number
US08673910B2

Reaction notes

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