Trifluoroacetic acid → 5'-Chloro-[2,2']bithiophenyl-5-sulfonic acid [2-oxo-1-(1H-pyrrolo[3,2-c]pyridin-2-ylmethyl)-pyrrolidin-3(S)-yl]-amide

HRID 651674

Reaktionsgleichung

Reaktionsgleichung von HRID 651674
FC(F)(F)C(O)=O.C(OC([N:15]1[C:23]2[CH:22]=[CH:21][N:20]=[CH:19][C:18]=2[CH:17]=[C:16]1[CH2:24][N:25]1[CH2:29][CH2:28][C@H:27]([NH:30][S:31]([C:34]2[S:38][C:37]([C:39]3[S:40][C:41]([Cl:44])=[CH:42][CH:43]=3)=[CH:36][CH:35]=2)(=[O:33])=[O:32])[C:26]1=[O:45])=O)(C)(C)C>C(Cl)Cl>[O:45]=[C:26]1[C@@H:27]([NH:30][S:31]([C:34]2[S:38][C:37]([C:39]3[S:40][C:41]([Cl:44])=[CH:42][CH:43]=3)=[CH:36][CH:35]=2)(=[O:33])=[O:32])[CH2:28][CH2:29][N:25]1[CH2:24][C:16]1[NH:15][C:23]2[CH:22]=[CH:21][N:20]=[CH:19][C:18]=2[CH:17]=1

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 697092092-[3-(S)-(5'-Chloro-[2,2']bithiophenyl-5-sulfonylamino)-2-oxo-pyrrolidin-1-ylmethyl]pyrrolo[3,2-c]pyridine-1-carboxylic acid tert-butyl ester

Produkt 1

HCID 100744105'-Chloro-[2,2']bithiophenyl-5-sulfonic acid [2-oxo-1-(1H-pyrrolo[3,2-c]pyridin-2-ylmethyl)-pyrrolidin-3(S)-yl]-amide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Trifluoroacetic acid (1.0 mL, 13.0 mol) is added dropwise to a slurry of 2-[3-(S)-(5′-chloro-[2,2′]bithiophenyl-5-sulfonylamino)-2-oxo-pyrrolidin-1-ylmethyl]pyrrolo[3,2-c]pyridine-1-carboxylic acid tert-butyl ester (0.13 g, 0.22 mmol) in CH2Cl2 (2 mL) at 0° C. After 30 min. the ice bath is removed and the solution is stirred at room temperature for 4 h. The reaction mixture is concentrated to dryness and the crude product is purified by RP-HPLC eluting in a gradient of 10% CH3CN/H2O (0.1% TFA) to 100% CH3CN. The appropriate product fractions are lyophilized to provide the title compound as a white solid.

Aufarbeitung

  1. customAfter 30 min. the ice bath is removed
  2. concentrationThe reaction mixture is concentrated to dryness
  3. customthe crude product is purified by RP-HPLC
  4. washeluting in a gradient of 10% CH3CN/H2O (0.1% TFA) to 100% CH3CN

Quellen und Nachweise

ORD-Eintrag
ord-7b96fa22b99a42fab51c7669a533defd
Quelldatensatz
uspto-grants-2001_08
Patentnummer
US06281227B1

Verknüpfte Notizen

Wird geladen…