Tetrahydrofuran → 2-(2-Chloroethoxy)-4-(4-methylpiperazin-1-yl)-6-(naphthalene-1-sulfonylmethyl)phenylamine

HRID 2219011Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2219011
[Cl:1][CH2:2][CH2:3][O:4][C:5]1[CH:6]=[C:7]([N:28]2[CH2:33][CH2:32][N:31]([CH3:34])[CH2:30][CH2:29]2)[CH:8]=[C:9]([CH2:14][S:15]([C:18]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH:21]=[CH:20][CH:19]=2)(=[O:17])=[O:16])[C:10]=1[N+:11]([O-])=O.C1COCC1>[Pd].CO>[Cl:1][CH2:2][CH2:3][O:4][C:5]1[CH:6]=[C:7]([N:28]2[CH2:29][CH2:30][N:31]([CH3:34])[CH2:32][CH2:33]2)[CH:8]=[C:9]([CH2:14][S:15]([C:18]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH:21]=[CH:20][CH:19]=2)(=[O:17])=[O:16])[C:10]=1[NH2:11]

Komponenten

5

Edukt 2

HCID 8028TetrahydrofuranHCID 598427971-[3-(2-Chloroethoxy)-5-(naphthalene-1-sulfonylmethyl)-4-nitrophenyl]-4-methylpiperazine

Produkt 1

HCID 598427982-(2-Chloroethoxy)-4-(4-methylpiperazin-1-yl)-6-(naphthalene-1-sulfonylmethyl)phenylamine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of 1-[3-(2-chloroethoxy)-5-(naphthalene-1-sulfonylmethyl)-4-nitrophenyl]-4-methylpiperazine (0.45 g, 0.85 mmoles) and 10% Pd/C in a 1:1 mixture of THF and methanol was hydrogenated on a Parr hydrogenator at 40 lb/in2 for 20 hours. The reaction mixture was filtered through Celite. The filtrate was diluted with EtOAc, washed with water, dried over Na2SO4, and concentrated under vacuum to afford the title compound as an off white solid (0.4 g, 0.82 mmoles), identified by HNMR and mass spectral analyses.

Aufarbeitung

  1. filtrationThe reaction mixture was filtered through Celite
  2. additionThe filtrate was diluted with EtOAc
  3. washwashed with water
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-b0f5c5bfda234b9e86780698ad0f6bc2
Quelldatensatz
uspto-grants-2008_08
Patentnummer
US07414051B2

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