Triethylamine → 7-Methoxy-naphthalene-2-sulfonic acid[1-(1-chloro-isoquinolin-7-ylmethyl)-2-oxopyrrolidin-3-(s)-yl]-amide

HRID 651596

Reaktionsgleichung

Reaktionsgleichung von HRID 651596
Cl.[NH2:2][C@H:3]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:18]=[C:17]3[C:12]([CH:13]=[CH:14][N:15]=[C:16]3[Cl:19])=[CH:11][CH:10]=2)[C:4]1=[O:20].C(N(CC)CC)C.[CH3:28][O:29][C:30]1[CH:39]=[C:38]2[C:33]([CH:34]=[CH:35][C:36]([S:40](Cl)(=[O:42])=[O:41])=[CH:37]2)=[CH:32][CH:31]=1>CC#N>[Cl:19][C:16]1[C:17]2[C:12](=[CH:11][CH:10]=[C:9]([CH2:8][N:5]3[CH2:6][CH2:7][C@H:3]([NH:2][S:40]([C:36]4[CH:35]=[CH:34][C:33]5[C:38](=[CH:39][C:30]([O:29][CH3:28])=[CH:31][CH:32]=5)[CH:37]=4)(=[O:42])=[O:41])[C:4]3=[O:20])[CH:18]=2)[CH:13]=[CH:14][N:15]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 105152667-methoxynaphthalene-2-sulfonyl ChlorideHCID 206807083-(S)-Amino-1-(1-chloro-isoquinolin-7-ylmethyl)-pyrrolidin-2-one hydrochloride

Produkt 1

HCID 155458317-Methoxy-naphthalene-2-sulfonic acid[1-(1-chloro-isoquinolin-7-ylmethyl)-2-oxopyrrolidin-3-(s)-yl]-amideAusbeute 96,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

3-(S)-Amino-1-(1-chloro-isoquinolin-7-ylmethyl)-pyrrolidin-2-one hydrochloride (1.74 g, 5.6 mmol) is suspended in CH3CN (120 mL). To this solution is added triethylamine (2.35 mL, 16.9 mmol) followed by 7-methoxynaphthalene-2-sulfonyl chloride (1.52 g, 5.93 mmol). The mixture is stirred overnight, then concentrated to dryness. The crude product is purified by column chromatography eluting with a gradient of 2% MeOH/CH2Cl2 to 5% MeOH/CH2Cl2 to give the title compound (2.7 g, 5.4 mmol) as a light yellow solid.

Aufarbeitung

  1. concentrationconcentrated to dryness
  2. customThe crude product is purified by column chromatography
  3. washeluting with a gradient of 2% MeOH/CH2Cl2 to 5% MeOH/CH2Cl2

Quellen und Nachweise

ORD-Eintrag
ord-08f798de8cd14bdfa44f05c7f1b9e960
Quelldatensatz
uspto-grants-2001_08
Patentnummer
US06281227B1

Verknüpfte Notizen

Wird geladen…