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Trifluoroacetic acid → 2-[5-chloro-1-(p-tolylsulfonyl)pyrrolo[2,3-b]pyridin-3-yl]-5-fluoro-N-[(3S)-3-piperidyl]pyrimidin-4-amine

HRID 526870
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 526870
[Cl:1][C:2]1[CH:3]=[C:4]2[C:10]([C:11]3[N:16]=[C:15]([NH:17][C@H:18]4[CH2:23][CH2:22][CH2:21][N:20](C(OC(C)(C)C)=O)[CH2:19]4)[C:14]([F:31])=[CH:13][N:12]=3)=[CH:9][N:8]([S:32]([C:35]3[CH:40]=[CH:39][C:38]([CH3:41])=[CH:37][CH:36]=3)(=[O:34])=[O:33])[C:5]2=[N:6][CH:7]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]2[C:10]([C:11]3[N:16]=[C:15]([NH:17][C@H:18]4[CH2:23][CH2:22][CH2:21][NH:20][CH2:19]4)[C:14]([F:31])=[CH:13][N:12]=3)=[CH:9][N:8]([S:32]([C:35]3[CH:40]=[CH:39][C:38]([CH3:41])=[CH:37][CH:36]=3)(=[O:34])=[O:33])[C:5]2=[N:6][CH:7]=1
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Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 68007804(S)-tert-butyl 3-(2-(5-chloro-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoropyrimidin-4-ylamino)piperidine-1-carboxylate2×

Produkt 1

HCID 672851192-[5-chloro-1-(p-tolylsulfonyl)pyrrolo[2,3-b]pyridin-3-yl]-5-fluoro-N-[(3S)-3-piperidyl]pyrimidin-4-amine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of tert-butyl (3S)-3-[[2-[5-chloro-1-(p-tolylsulfonyl)pyrrolo[5,4-b]pyridin-3-yl]-5-fluoro-pyrimidin-4-yl]amino]piperidine-1-carboxylate, 1b, (2.1 g, 3.5 mmol) in CH2Cl2 (30 mL) was added trifluoroacetic acid (20 mL). After stirring the reaction mixture at room temperature for 75 min, the mixture was concentrated under vacuo. The crude residue was diluted with EtOAc and neutralized with 1N sodium hydroxide solution. The aqueous phase was separated and extracted again with EtOAc. The combined organic phases were dried (MgSO4), filtered and concentrated under vacuo to afford the desired product (1c) as a light yellow solid.

Aufarbeitung

  1. concentrationthe mixture was concentrated under vacuo
  2. additionThe crude residue was diluted with EtOAc and neutralized with 1N sodium hydroxide solution
  3. customThe aqueous phase was separated
  4. extractionextracted again with EtOAc
  5. dry with materialThe combined organic phases were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated under vacuo

Quellen und Nachweise

ORD-Eintrag
ord-55f94b42e7f441fcb05527a859bf136e
Quelldatensatz
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09345708B2

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