Water → 6-(2,6-Dimethoxyphenyl)-1-(quinolin-3-ylmethyl)piperidin-2-one

HRID 594386

Reaktionsgleichung

Reaktionsgleichung von HRID 594386
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH3:10])[C:4]=1[CH:11]([NH:18][CH2:19][C:20]1[CH:21]=[N:22][C:23]2[C:28]([CH:29]=1)=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:12][CH2:13][CH2:14][C:15]([OH:17])=O.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.O>CN(C=O)C.CCOCC>[CH3:10][O:9][C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[C:4]=1[CH:11]1[N:18]([CH2:19][C:20]2[CH:21]=[N:22][C:23]3[C:28]([CH:29]=2)=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:15](=[O:17])[CH2:14][CH2:13][CH2:12]1

Komponenten

7

Edukt 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 690835275-(2,6-Dimethoxyphenyl)-5-((quinolin-3-ylmethyl)amino)pentanoic acid

Produkt 1

HCID 690841526-(2,6-Dimethoxyphenyl)-1-(quinolin-3-ylmethyl)piperidin-2-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A yellow solution of 5-(2,6-dimethoxyphenyl)-5-((quinolin-3-ylmethyl)amino)pentanoic acid (1.074 g; 2.72 mmol; 1.0 equiv.) in anh. DMF (50 ml) was treated successively with HATU (1.294 g; 3.40 mmol; 1.25 equiv.) and with DIPEA (0.59 ml; 3.40 mmol; 1.25 equiv.). The resulting orange solution was stirred at rt, under nitrogen, for 2 h45. Water (100 ml) and Et2O (100 ml) were then added, and the separated aq. layer was further extracted with Et2O (3×100 ml). The mixed organic layers were washed with water (15 ml) and with brine (15 ml), dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure. Purification by FC (DCM/MeOH=20/1) afforded 6-(2,6-dimethoxyphenyl)-1-(quinolin-3-ylmethyl)piperidin-2-one as a beige solid. LC-MS (conditions B): tR=0.68 min.; [M+H]+: 377.36 g/mol.

Aufarbeitung

  1. extractionthe separated aq. layer was further extracted with Et2O (3×100 ml)
  2. washThe mixed organic layers were washed with water (15 ml) and with brine (15 ml)
  3. dry with materialdried over anh. MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated to dryness under reduced pressure
  6. customPurification by FC (DCM/MeOH=20/1)

Quellen und Nachweise

ORD-Eintrag
ord-29b83cfe6d604eb1ac04533905f7b07a
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09242970B2

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