5-Pyridin-4-yl-thiophene-2-sulfonyl chloride → 5-Pyridin-4-yl-thiophene-2-sulfonic acid-[1-(1-chloro-isoquinolin-7-ylmethyl)-2-oxopyrrolidin-3-(s)-yl]-amide

HRID 651637

Reaktionsgleichung

Reaktionsgleichung von HRID 651637
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[S:11][C:10]([S:12](Cl)(=[O:14])=[O:13])=[CH:9][CH:8]=2)=[CH:3][CH:2]=1.Cl.[NH2:17][C@H:18]1[CH2:22][CH2:21][N:20]([CH2:23][C:24]2[CH:33]=[C:32]3[C:27]([CH:28]=[CH:29][N:30]=[C:31]3[Cl:34])=[CH:26][CH:25]=2)[C:19]1=[O:35]>N1C=CC=CC=1>[Cl:34][C:31]1[C:32]2[C:27](=[CH:26][CH:25]=[C:24]([CH2:23][N:20]3[CH2:21][CH2:22][C@H:18]([NH:17][S:12]([C:10]4[S:11][C:7]([C:4]5[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=5)=[CH:8][CH:9]=4)(=[O:14])=[O:13])[C:19]3=[O:35])[CH:33]=2)[CH:28]=[CH:29][N:30]=1

Komponenten

4

Edukt 2

HCID 106350455-Pyridin-4-yl-thiophene-2-sulfonyl chlorideHCID 206807083-(S)-Amino-1-(1-chloro-isoquinolin-7-ylmethyl)-pyrrolidin-2-one hydrochloride

Produkt 1

HCID 206807365-Pyridin-4-yl-thiophene-2-sulfonic acid-[1-(1-chloro-isoquinolin-7-ylmethyl)-2-oxopyrrolidin-3-(s)-yl]-amide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

5-Pyridin-4-yl-thiophene-2-sulfonyl chloride is added to a solution of 3-(S)-amino-1-(1-chloro-isoquinolin-7-ylmethyl)-pyrrolidin-2-one hydrochloride (0.12 g, 0.38 mmol) in pyridine (2 mL). The resulting mixture is stirred 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 and concentrated to give 105 mg of a crude solid. The crude product is purified by column chromatography eluting with 5% MeOH/CH2Cl2 to afford the title product (0.026 g, 0.052 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. customto give 105 mg of a crude solid
  8. customThe crude product is purified by column chromatography
  9. washeluting with 5% MeOH/CH2Cl2

Quellen und Nachweise

ORD-Eintrag
ord-61a4ae5177384a0aa1b856c2e173fc7c
Quelldatensatz
uspto-grants-2001_08
Patentnummer
US06281227B1

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