Water → 4-(5-Dimethylamino-naphthalene-1-sulfonyl)-piperazin-1-yl-thiazole-5-carboxylic acid methyl ester

HRID 1392952

Reaktionsgleichung

Reaktionsgleichung von HRID 1392952
[CH3:1][O:2][C:3]([C:5]1[S:9][C:8]([N:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[N:7][CH:6]=1)=[O:4].[CH3:16][N:17]([CH3:32])[C:18]1[CH:27]=[CH:26][CH:25]=[C:24]2[C:19]=1[CH:20]=[CH:21][CH:22]=[C:23]2[S:28](Cl)(=[O:30])=[O:29].C(N(CC)CC)C.O>ClCCl>[CH3:1][O:2][C:3]([C:5]1[S:9][C:8]([N:10]2[CH2:11][CH2:12][N:13]([S:28]([C:23]3[C:24]4[C:19](=[C:18]([N:17]([CH3:32])[CH3:16])[CH:27]=[CH:26][CH:25]=4)[CH:20]=[CH:21][CH:22]=3)(=[O:30])=[O:29])[CH2:14][CH2:15]2)=[N:7][CH:6]=1)=[O:4]

Komponenten

6

Edukt 4

HCID 962WaterHCID 8471TriethylamineHCID 11801Dansyl chlorideHCID 22831866Methyl 2-(piperazin-1-yl)thiazole-5-carboxylate

Produkt 1

HCID 691997234-(5-Dimethylamino-naphthalene-1-sulfonyl)-piperazin-1-yl-thiazole-5-carboxylic acid methyl esterAusbeute 57,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of compound 11 (200 mg, 0.886 mmol) in dichloromethane (7.5 mL) were added 5-dimethylamino-naphthalene-1-sulfonyl chloride (356 mg, 1.320 mmol) and triethylamine (220 mg, 2.169 mmol) under N2 atmosphere. The reaction mixture was stirred at room temperature for 4 h. Water (10 mL) followed by dichloromethane (10 mL) were added to the reaction mixture and the organic layer was separated, dried on sodium sulphate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography using silica gel to give the compound 12k as a solid (233 mg, 57.50%). HPLC: 99.04% (Rt=12.33 min).

Aufarbeitung

  1. additionwere added to the reaction mixture
  2. customthe organic layer was separated
  3. customdried on sodium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-57c60e8e0d7e41729601ec3fe0b50540
Quelldatensatz
uspto-grants-2008_03
Patentnummer
US07345043B2

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