tert-butyl (S)-3-methyl-1-((S)-2,2,2-trifluoro-1-(6-hydrazinylpyridin-3-yl)ethyl)pyrrolidin-3-ylcarbamate → tert-butyl N-[(3S)-3-methyl-1-[(1S)-2,2,2-trifluoro-1-[6-[(2E)-2-[(6-fluoro-8-methoxyquinolin-2-yl)methylidene]hydrazinyl]pyridin-3-yl]ethyl]pyrrolidin-3-yl]carbamate

HRID 339027Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 339027
[CH3:1][C@:2]1([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[CH2:6][CH2:5][N:4]([C@@H:7]([C:12]2[CH:13]=[N:14][C:15]([NH:18][NH2:19])=[CH:16][CH:17]=2)[C:8]([F:11])([F:10])[F:9])[CH2:3]1.[F:28][C:29]1[CH:30]=[C:31]2[C:36](=[C:37]([O:39][CH3:40])[CH:38]=1)[N:35]=[C:34]([CH:41]=O)[CH:33]=[CH:32]2>C(Cl)Cl>[CH3:1][C@:2]1([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[CH2:6][CH2:5][N:4]([C@@H:7]([C:12]2[CH:13]=[N:14][C:15]([NH:18]/[N:19]=[CH:41]/[C:34]3[CH:33]=[CH:32][C:31]4[C:36](=[C:37]([O:39][CH3:40])[CH:38]=[C:29]([F:28])[CH:30]=4)[N:35]=3)=[CH:16][CH:17]=2)[C:8]([F:9])([F:10])[F:11])[CH2:3]1

Komponenten

4

Edukt 2

HCID 86707435tert-butyl (S)-3-methyl-1-((S)-2,2,2-trifluoro-1-(6-hydrazinylpyridin-3-yl)ethyl)pyrrolidin-3-ylcarbamateHCID 867074476-Fluoro-8-methoxyquinoline-2-carbaldehyde

Produkt 1

HCID 140628987tert-butyl N-[(3S)-3-methyl-1-[(1S)-2,2,2-trifluoro-1-[6-[(2E)-2-[(6-fluoro-8-methoxyquinolin-2-yl)methylidene]hydrazinyl]pyridin-3-yl]ethyl]pyrrolidin-3-yl]carbamateAusbeute 76,45 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of tert-butyl (S)-3-methyl-1-((S)-2,2,2-trifluoro-1-(6-hydrazinylpyridin-3-yl)ethyl)pyrrolidin-3-ylcarbamate (1.00 g, 2.57 mmol) in DCM (15 mL) was added 6-fluoro-8-methoxyquinoline-2-carbaldehyde (0.5269 g, 2.568 mmol) and the reaction mixture was stirred at ambient temperature overnight. The reaction was concentrated under reduced pressure and the residue purified by chromatography (C18, 300 g, 10% MeCN/water to 95% MeCN/water over 25 column volumes) to give tert-butyl (S)-3-methyl-1-((S)-2,2,2-trifluoro-1-(6-((E)-2-((6-fluoro-8-methoxyquinolin-2-yl)methylene)hydrazinyl)pyridin-3-yl)ethyl)pyrrolidin-3-ylcarbamate (1.132 g, 1.963 mmol, 76.45% yield).

Aufarbeitung

  1. concentrationThe reaction was concentrated under reduced pressure
  2. customthe residue purified by chromatography (C18, 300 g, 10% MeCN/water to 95% MeCN/water over 25 column volumes)

Quellen und Nachweise

ORD-Eintrag
ord-529f83391d004af6ae98b51f3f0c9f73
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08889704B2

Notizen zur Reaktion

Wird geladen…