N-(3-(2-hydroxyethylthio)-4-oxonaphthalen-1(4H)-ylidene)thiophene-2-sulfonamide → N-(4-hydroxy-3-(1-methyl-1H-tetrazol-5-ylthio)naphthalen-1-yl)thiophene-2-sulfonamide

HRID 1258393Notes

Reaction equation

HRID 1258393 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:25]=[N:24][N:23]=1.[OH:28][CH2:29][CH2:30][S:31][C:32]1[C:41](=[O:42])[C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[C:34](=[N:43][S:44]([C:47]2[S:48][CH:49]=[CH:50][CH:51]=2)(=[O:46])=[O:45])[CH:33]=1>>[OH:42][C:41]1[C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[C:34]([NH:43][S:44]([C:47]2[S:48][CH:49]=[CH:50][CH:51]=2)(=[O:46])=[O:45])=[CH:33][C:32]=1[S:31][CH2:30][CH2:29][OH:28].[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:25]=[N:24][N:23]=1

Participants

4

Reactant 2

HCID 67330679N-(3-(2-hydroxyethylthio)-4-oxonaphthalen-1(4H)-ylidene)thiophene-2-sulfonamideHCID 135895396N-(4-hydroxy-3-(1-methyl-1H-tetrazol-5-ylthio)naphthalen-1-yl)thiophene-2-sulfonamide

Product 2

HCID 46908187N-(4-hydroxy-3-(2-hydroxyethylthio)naphthalen-1-yl)thiophene-2-sulfonamideHCID 135895396N-(4-hydroxy-3-(1-methyl-1H-tetrazol-5-ylthio)naphthalen-1-yl)thiophene-2-sulfonamideYield 53.1%

Procedure

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-756bcc9f546e4df2b821732c1470d85f
Source dataset
uspto-grants-2013_06
Patent number
US08466157B2

Reaction notes

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