Triethylamine → 5-Pyridin-3-yl-thiophene-2-sulfonic acid-[1-(1-chloro-isoquinolin-7-ylmethyl)-2-oxopyrrolidin-3-(S)-yl]-amide

HRID 651638

Reaktionsgleichung

Reaktionsgleichung von HRID 651638
C(N(CC)CC)C.[N:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]2[S:18][C:17]([S:19](Cl)(=[O:21])=[O:20])=[CH:16][CH:15]=2)[CH:9]=1.Cl.[NH2:24][C@H:25]1[CH2:29][CH2:28][N:27]([CH2:30][C:31]2[CH:40]=[C:39]3[C:34]([CH:35]=[CH:36][N:37]=[C:38]3[Cl:41])=[CH:33][CH:32]=2)[C:26]1=[O:42]>CC#N>[Cl:41][C:38]1[C:39]2[C:34](=[CH:33][CH:32]=[C:31]([CH2:30][N:27]3[CH2:28][CH2:29][C@H:25]([NH:24][S:19]([C:17]4[S:18][C:14]([C:10]5[CH:9]=[N:8][CH:13]=[CH:12][CH:11]=5)=[CH:15][CH:16]=4)(=[O:21])=[O:20])[C:26]3=[O:42])[CH:40]=2)[CH:35]=[CH:36][N:37]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 106589765-Pyridin-3-yl-thiophene-2-sulfonyl chlorideHCID 206807083-(S)-Amino-1-(1-chloro-isoquinolin-7-ylmethyl)-pyrrolidin-2-one hydrochloride

Produkt 1

HCID 206807355-Pyridin-3-yl-thiophene-2-sulfonic acid-[1-(1-chloro-isoquinolin-7-ylmethyl)-2-oxopyrrolidin-3-(S)-yl]-amideAusbeute 63,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

Triethylamine (0.35 mL, 2.5 mmol) is added dropwise to a solution of 5-pyridin-3-yl-thiophene-2-sulfonyl chloride (0.22 g, 0.85 mmol) and 3-(S)-amino-1-(1-chloro-isoquinolin-7-ylmethyl)-pyrrolidin-2-one hydrochloride (0.22 g, 0.71 mmol) in CH3CN (5 mL). The suspension is stirred at room temperature overnight then concentrated to dryness. The residue is diluted with methylene chloride and washed with saturated NaHCO3 solution and brine. The organic layer is dried over MgSO4, filtered, concentrated, and then purified by column chromatography eluting with a gradient of 1% MeOH/CH2Cl2 to 5% MeOH/CH2Cl2 to give the product (0.23 g, 0.45 mmol) as a white solid.

Aufarbeitung

  1. concentrationthen concentrated to dryness
  2. additionThe residue is diluted with methylene chloride
  3. washwashed with saturated NaHCO3 solution and brine
  4. dry with materialThe organic layer is dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by column chromatography
  8. washeluting with a gradient of 1% MeOH/CH2Cl2 to 5% MeOH/CH2Cl2

Quellen und Nachweise

ORD-Eintrag
ord-cc7df4c7111441acb5f91233ac9d297f
Quelldatensatz
uspto-grants-2001_08
Patentnummer
US06281227B1

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