Hydrazine → 3-Amino-N-[4-(3-aminocyclohexyl)pyridin-3-yl]-7-ethylquinoline-2-carboxamide

HRID 924412Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 924412
[NH2:1][C:2]1[C:3]([C:14]([OH:16])=O)=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[C:7]([CH2:12][CH3:13])[CH:6]=2.[NH2:17][C:18]1[CH:19]=[N:20][CH:21]=[CH:22][C:23]=1[CH:24]1[CH2:29][CH2:28][CH2:27][CH:26]([N:30]2C(=O)C3C(=CC=CC=3)C2=O)[CH2:25]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+].NN>CN(C=O)C.CO>[NH2:1][C:2]1[C:3]([C:14]([NH:17][C:18]2[CH:19]=[N:20][CH:21]=[CH:22][C:23]=2[CH:24]2[CH2:29][CH2:28][CH2:27][CH:26]([NH2:30])[CH2:25]2)=[O:16])=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[C:7]([CH2:12][CH3:13])[CH:6]=2

Komponenten

9

Edukt 6

HCID 9321HydrazineHCID 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 59226443HCID 59226443, VerbindungHCID 867268773-Amino-7-ethylquinoline-2-carboxylic acid

Produkt 1

HCID 778440263-Amino-N-[4-(3-aminocyclohexyl)pyridin-3-yl]-7-ethylquinoline-2-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

A mixture of 3-amino-7-ethylquinoline-2-carboxylic acid (0.040 g, 0.18 mmol), 2-[3-(3-aminopyridin-4-yl)cyclohexyl]-1H-isoindole-1,3(2H)-dione (0.055 g, 0.17 mmol), HATU (0.22 g, 0.58 mmol), DMF (0.65 mL) and DIPEA (0.076 g, 0.59 mmol) was stirred at room temperature for 16 h. Aq. NaOH (1 M) was added to the reaction mixture, and a precipitate formed, which was collected by vacuum filtration. The collected solid was washed with 1 M NaOH, followed by water and dried under vacuum to afford an intermediate. The intermediate was dissolved in DMF (0.15 mL) and hydrazine (0.15 mL) was added. The resulting reaction mixture was stirred at room temperature for 16 h, diluted with MeOH, filtered and purified by preparative LC MS (XBridge™ preparative C18 5 μm 30×10 mm OBD™ column, flow rate 60 mL/min., eluting with a gradient of MeCN and water with 0.15% NH4OH) to give title compound. LCMS calc. for C23H28N5O (M+H)+: m/z=390.2. Found: 390.1.

Aufarbeitung

  1. customa precipitate formed
  2. filtrationwhich was collected by vacuum filtration
  3. washThe collected solid was washed with 1 M NaOH
  4. customdried under vacuum
  5. customto afford an intermediate
  6. customThe resulting reaction mixture
  7. stirringwas stirred at room temperature for 16 h
  8. filtrationfiltered
  9. custompurified by preparative LC MS (XBridge™ preparative C18 5 μm 30×10 mm OBD™ column, flow rate 60 mL/min.
  10. washeluting with a gradient of MeCN and water with 0.15% NH4OH)

Quellen und Nachweise

ORD-Eintrag
ord-d6bef013f78a4cb2a31fb30abe8712eb
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09278950B2

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