Hydrochloric Acid → (E)-N-Hydroxy-3-{1-[4-(1-methyl-1H-indol-5-yl)-benzenesulfonyl]-1H-pyrrol-3-yl}-acrylamide

HRID 2408433Notes

Reaction equation

HRID 2408433 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([C:11]3[CH:16]=[CH:15][C:14]([S:17]([N:20]4[CH:24]=[CH:23][C:22](/[CH:25]=[CH:26]/[C:27]([NH:29][O:30]C5CCCCO5)=[O:28])=[CH:21]4)(=[O:19])=[O:18])=[CH:13][CH:12]=3)=[CH:8][CH:9]=2)[CH:4]=[CH:3]1.Cl>CO>[OH:30][NH:29][C:27](=[O:28])/[CH:26]=[CH:25]/[C:22]1[CH:23]=[CH:24][N:20]([S:17]([C:14]2[CH:13]=[CH:12][C:11]([C:7]3[CH:6]=[C:5]4[C:10](=[CH:9][CH:8]=3)[N:2]([CH3:1])[CH:3]=[CH:4]4)=[CH:16][CH:15]=2)(=[O:19])=[O:18])[CH:21]=1

Participants

4

Reactant 2

HCID 313Hydrochloric Acid2×HCID 86621684(E)-3-{1-[4-(1-methyl-1H-indol-5-yl)-benzenesulfonyl]-1H-pyrrol-3-yl}-N-(tetrahydro-pyran-2-yloxy)-acrylamide

Product 1

HCID 11640386(E)-N-Hydroxy-3-{1-[4-(1-methyl-1H-indol-5-yl)-benzenesulfonyl]-1H-pyrrol-3-yl}-acrylamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 0.346 g (E)-3-{1-[4-(1-methyl-1H-indol-5-yl)-benzenesulfonyl]-1H-pyrrol-3-yl}-N-(tetrahydro-pyran-2-yloxy)-acrylamide with 20 ml methanol and 13.9 ml 0.5M aqueous HCl is stirred at ambient temperature for 24 h. The crude product is isolated and in case of incomplete deprotection the resulted mixture is treated again with 1 N aqueous HCl until the reaction is at completion. The crude product is isolated by evaporation and the title compound is isolated by prep-HPLC chromatography using an ammonium formiate gradient. By this method 0.047 g of the title compound are obtained.

Workup

  1. customThe crude product is isolated and in case of incomplete deprotection the resulted mixture
  2. customThe crude product is isolated by evaporation

Sources & evidence

ORD record
ord-224ac2db04de4c059fbc5ebc5fa6f810
Source dataset
uspto-grants-2014_08
Patent number
US08815855B2

Reaction notes

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