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Oxalyl chloride → 4-[2-(Benzofurazan-5-yl)ethyl]-1-(indole-5-carbonyl)piperazine

HRID 1195677
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1195677
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]([OH:12])=O)=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.C(Cl)(=O)C(Cl)=O.[N:19]1[O:23][N:22]=[C:21]2[CH:24]=[C:25]([CH2:28][CH2:29][N:30]3[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]3)[CH:26]=[CH:27][C:20]=12.C(N(C(C)C)CC)(C)C>C1COCC1.CN(C=O)C.ClCCl>[N:19]1[O:23][N:22]=[C:21]2[CH:24]=[C:25]([CH2:28][CH2:29][N:30]3[CH2:31][CH2:32][N:33]([C:10]([C:6]4[CH:5]=[C:4]5[C:9](=[CH:8][CH:7]=4)[NH:1][CH:2]=[CH:3]5)=[O:12])[CH2:34][CH2:35]3)[CH:26]=[CH:27][C:20]=12
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 65578Oxalyl chlorideHCID 742801H-Indole-5-Carboxylic AcidHCID 81531DiisopropylethylamineHCID 151663825-(2-Piperazin-1-ylethyl)-2,1,3-benzoxadiazole

Produkt 1

HCID 151663954-[2-(Benzofurazan-5-yl)ethyl]-1-(indole-5-carbonyl)piperazine

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6228
Dimethylformamide
Katalysator
HCID 6344DichloromethaneLösungsmittel
HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Indole-5-carboxylic acid (57 mg, 0.35 mmol) was dissolved in THF (2 ml) and DMF (1 drop), then oxalyl chloride (37 μl, 54 mg, 0.42 mmol) was added. The mixture was stirred at room temperature for 3 hours, the solvent was evaporated under reduced pressure and the residue was dissolved in DMF (2 ml) and added to a stirred solution of 1-[2-(benzofurazan-5-yl)ethyl]piperazine (81 mg, 0.35 mmol) and diisopropylethylamine (91 μl, 68 mg, 0.52 mmol) in dichloromethane (1 ml). The mixture was stirred at room temperature for 24 hours, then the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel, eluting with CH2Cl2 /CH3OH/NH3 ; 96:4:0.4 and crystallized from ethyl acetate/CHCl3 /hexane to give the piperazine as yellow microcrystals (16 mg, 12%), mp 180°-183° C.

Aufarbeitung

  1. customthe solvent was evaporated under reduced pressure
  2. dissolutionthe residue was dissolved in DMF (2 ml)
  3. stirringThe mixture was stirred at room temperature for 24 hours
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by flash column chromatography on silica gel
  6. washeluting with CH2Cl2 /CH3OH/NH3
  7. custom96:4:0.4 and crystallized from ethyl acetate/CHCl3 /hexane

Quellen und Nachweise

ORD-Eintrag
ord-c929f49f7a3c4bd08781344c509356af
Quelldatensatz
uspto-grants-1992_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05112824

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