Sodium Hydroxide → Benzyl (2-{[(4-{(3S)-3-[(tert-butoxycarbonyl)amino]piperidin-1-yl}pyridin-3-yl)amino]carbonyl}-7-vinylquinolin-3-yl)carbamate

HRID 924387Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 924387
[CH2:1]([O:8][C:9]([NH:11][C:12]1[C:13]([C:24](O)=[O:25])=[N:14][C:15]2[C:20]([CH:21]=1)=[CH:19][CH:18]=[C:17]([CH:22]=[CH2:23])[CH:16]=2)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:27][C:28]1[CH:29]=[N:30][CH:31]=[CH:32][C:33]=1[N:34]1[CH2:39][CH2:38][CH2:37][C@H:36]([NH:40][C:41](=[O:47])[O:42][C:43]([CH3:46])([CH3:45])[CH3:44])[CH2:35]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[OH-].[Na+]>CN(C=O)C>[C:43]([O:42][C:41]([NH:40][C@H:36]1[CH2:37][CH2:38][CH2:39][N:34]([C:33]2[CH:32]=[CH:31][N:30]=[CH:29][C:28]=2[NH:27][C:24]([C:13]2[C:12]([NH:11][C:9](=[O:10])[O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[CH:21][C:20]3[C:15](=[CH:16][C:17]([CH:22]=[CH2:23])=[CH:18][CH:19]=3)[N:14]=2)=[O:25])[CH2:35]1)=[O:47])([CH3:44])([CH3:46])[CH3:45]

Komponenten

7

Edukt 5

HCID 14798Sodium HydroxideHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 59332360(S)-tert-Butyl (1-(3-aminopyridin-4-yl)piperidin-3-yl)carbamateHCID 867268683-{[(Benzyloxy)carbonyl]amino}-7-vinylquinoline-2-carboxylic acid

Produkt 1

HCID 86726869Benzyl (2-{[(4-{(3S)-3-[(tert-butoxycarbonyl)amino]piperidin-1-yl}pyridin-3-yl)amino]carbonyl}-7-vinylquinolin-3-yl)carbamateAusbeute 53 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

3-{[(Benzyloxy)carbonyl]amino}-7-vinylquinoline-2-carboxylic acid (0.55 g, 1.6 mmol) was mixed with tert-butyl [(3S)-1-(3-aminopyridin-4-yl)piperidin-3-yl]carbamate (0.46 g, 1.6 mmol), DMF (4.0 mL), HATU (1.2 g, 3.2 mmol) and DIPEA (1.1 mL, 6.3 mmol). The reaction mixture was stirred at room temperature for 16 h. Aq. NaOH (1 M, 20 mL) was then added to the reaction mixture. A precipitate formed, which was collected by vacuum filtration to give the sub-title compound (0.52 g, 53%) as light yellow powder. LCMS calc. for C35H39N6O5 (M+H)+: m/z=623.2. Found: 623.3.

Aufarbeitung

  1. customA precipitate formed
  2. filtrationwhich was collected by vacuum filtration

Quellen und Nachweise

ORD-Eintrag
ord-142192a37df84dbe941220b9ae8d489c
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09278950B2

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