2-Methoxyethylamine → methyl 5-[N-acetyl-N-(2-methoxyethyl)amino]-4,7-dihydro-6-(2-methoxyethyl)amino-4,7-dioxobenzo[b]thiophene-2-carboxylate

HRID 1582195Notes

Reaction equation

HRID 1582195 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][NH2:5].[C:6]([N:9]([C:14]1[C:15](=[O:28])[C:16]2[CH:20]=[C:19]([C:21]([O:23][CH3:24])=[O:22])[S:18][C:17]=2[C:25](=[O:27])[CH:26]=1)[CH2:10][CH2:11][O:12][CH3:13])(=[O:8])[CH3:7]>O1CCCC1>[C:6]([N:9]([C:14]1[C:15](=[O:28])[C:16]2[CH:20]=[C:19]([C:21]([O:23][CH3:24])=[O:22])[S:18][C:17]=2[C:25](=[O:27])[C:26]=1[NH:5][CH2:4][CH2:3][O:2][CH3:1])[CH2:10][CH2:11][O:12][CH3:13])(=[O:8])[CH3:7]

Participants

4

Reactant 2

HCID 80182-MethoxyethylamineHCID 12987500methyl 5-[N-acetyl-N-(2-methoxyethyl)amino]-4,7-dihydro-4,7-dioxobenzo[b]thiophene-2-carboxylate

Product 1

HCID 22719980methyl 5-[N-acetyl-N-(2-methoxyethyl)amino]-4,7-dihydro-6-(2-methoxyethyl)amino-4,7-dioxobenzo[b]thiophene-2-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-Methoxyethylamine (0.15 ml) was added to a solution of methyl 5-[N-acetyl-N-(2-methoxyethyl)amino]-4,7-dihydro-4,7-dioxobenzo[b]thiophene-2-carboxylate (0.39 g) in tetrahydrofuran (30 ml) and the mixture was stirred at room temperature for 6.5 hours. The solvent was evaporated and the residue was purified by silica gel column chromatography (elution with hexane-ethyl acetate 50:1 solution) to give methyl 5-[N-acetyl-N-(2-methoxyethyl)amino]-4,7-dihydro-6-(2-methoxyethyl)amino-4,7-dioxobenzo[b]thiophene-2-carboxylate (0.39 g) as a reddish purple oil.

Workup

  1. customThe solvent was evaporated
  2. customthe residue was purified by silica gel column chromatography (elution with hexane-ethyl acetate 50:1 solution)

Sources & evidence

ORD record
ord-e414575204514a368c714cc5f88fa0ae
Source dataset
uspto-grants-2004_05
Patent number
US06734203B2

Reaction notes

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