Diisopropylethylamine → 7-[4-(4-Chloro-phenyl)-piperazin-1-ylmethyl]-10-oxo-1,3,4,9,10,10a-hexahydro-2,4-a,5,9-tetraaza-phenanthrene-2-carboxylic acid tert-butyl ester

HRID 69675

Reaktionsgleichung

Reaktionsgleichung von HRID 69675
[C:1]([O:5][C:6]([N:8]1[CH2:21][CH2:20][N:19]2[CH:10]([C:11](=[O:24])[NH:12][C:13]3[C:18]2=[N:17][CH:16]=[C:15]([CH2:22]O)[CH:14]=3)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[I-].C(C[P+](C)(C)C)#N.C(N(C(C)C)C(C)C)C.Cl.[Cl:43][C:44]1[CH:49]=[CH:48][C:47]([N:50]2[CH2:55][CH2:54][NH:53][CH2:52][CH2:51]2)=[CH:46][CH:45]=1>C(#N)CC>[C:1]([O:5][C:6]([N:8]1[CH2:21][CH2:20][N:19]2[CH:10]([C:11](=[O:24])[NH:12][C:13]3[C:18]2=[N:17][CH:16]=[C:15]([CH2:22][N:53]2[CH2:52][CH2:51][N:50]([C:47]4[CH:46]=[CH:45][C:44]([Cl:43])=[CH:49][CH:48]=4)[CH2:55][CH2:54]2)[CH:14]=3)[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 30847201-(4-Chlorophenyl)piperazine HydrochlorideHCID 10514344(Cyanomethyl)trimethylphosphanium iodideHCID 583244417-Hydroxymethyl-10-oxo-1,3,4,9,10,10a-hexahydro-2,4-a,5,9-tetraaza-phenanthrene-2-carboxylic acid tert-butyl ester

Produkt 1

HCID 583243557-[4-(4-Chloro-phenyl)-piperazin-1-ylmethyl]-10-oxo-1,3,4,9,10,10a-hexahydro-2,4-a,5,9-tetraaza-phenanthrene-2-carboxylic acid tert-butyl esterAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7854PropionitrileLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

7-Hydroxymethyl-10-oxo-1,3,4,9,10,10a-hexahydro-2,4a,5,9-tetraaza-phenanthrene-2-carboxylic acid tert-butyl ester (22.0 mg, 0.598 mmol) was suspended in propionitrile (1.5 mL) and (cyanomethyl)trimethylphosphonium iodide (174.0 mg, 0.718 mmol) was added followed by N-ethyl-N-isopropylpropan-2-amine (313 ul, 1.794 mmol). To the stirred mixture was then added 1-(4-chlorophenyl)piperazine hydrochloride (139 mg, 0.598 mmol). The reaction was heated to 90° C. with stirring for 16 h. The crude reaction was cooled to room temperature and purified on silica column (24 g, 25% THF in ethyl acetate). The fractions were combined and concentrated to afford 250.9 mg (82%) of the title compound as a brown solid in 80% purity. [M+H] calc'd for C26H33ClN6O3, 513; found, 513.

Aufarbeitung

  1. customThe crude reaction
  2. temperaturewas cooled to room temperature
  3. custompurified on silica column (24 g, 25% THF in ethyl acetate)
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-7a0e1d4c21f44c328ad1a5ebe00c5468
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822470B2

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