Triethylamine → 3-Chloro-4-[4-(2-morpholin-4-yl-5-nitro-benzoyl)-piperazin-1-yl]-benzonitrile

HRID 736130

Reaktionsgleichung

Reaktionsgleichung von HRID 736130
[N:1]1([C:7]2[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][C:8]=2[C:9](Cl)=[O:10])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[Cl:19][C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][C:27]=1[N:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1)[C:23]#[N:24].CCN(CC)CC>C(Cl)Cl>[Cl:19][C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][C:27]=1[N:28]1[CH2:33][CH2:32][N:31]([C:9](=[O:10])[C:8]2[CH:12]=[C:13]([N+:16]([O-:18])=[O:17])[CH:14]=[CH:15][C:7]=2[N:1]2[CH2:6][CH2:5][O:4][CH2:3][CH2:2]2)[CH2:30][CH2:29]1)[C:23]#[N:24]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 172741532-Morpholin-4-yl-5-nitro-benzoyl chlorideHCID 193671133-Chloro-4-(piperazin-1-yl)benzonitrile

Produkt 1

HCID 597934973-Chloro-4-[4-(2-morpholin-4-yl-5-nitro-benzoyl)-piperazin-1-yl]-benzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of 40.6 mg (0.15 mmol) 2-Morpholin-4-yl-5-nitro-benzoyl chloride, 39.9 mg (0.18 mmol) 3-Chloro-4-piperazin-1-yl-benzonitrile (WO9625414) and 62.5 ul (0.45 mmol) NEt3 in 1 ml DCM was stirred at room temperature for 16 h. After evaporation of the volatiles the residue was taken up in 1 ml CH3CN/DMF/HCOOH 3/5/2 and subjected to preparative HPLC purification on reversed phase eluting with an acetonitrile/water gradient to yield after evaporation of the product fractions 4.9 mg (8%) of the title compound.

Aufarbeitung

  1. customAfter evaporation of the volatiles the residue
  2. customsubjected to preparative HPLC purification on reversed phase
  3. washeluting with an acetonitrile/water gradient
  4. customto yield
  5. customafter evaporation of the product fractions 4.9 mg (8%) of the title compound

Quellen und Nachweise

ORD-Eintrag
ord-a1d2d5aa77dd4f9aa603f00294c781e5
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07595314B2

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