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Pyridine → 6-(morpholin-4-yl)-2-{2-oxo-2-[4-(1-propylpiperidin-3-yl)-2,3-dihydro-1H-indol-1-yl]ethyl}pyrimidin-4(3H)-one

HRID 2278617
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Reaktionsgleichung

Reaktionsgleichung von HRID 2278617
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[N:8]1[C:13](=[O:14])[CH:12]=[C:11]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[N:10]=[C:9]1[CH2:21][C:22](=[O:36])[N:23]1[C:31]2[C:26](=[C:27](C(F)(F)F)[CH:28]=[CH:29][CH:30]=2)[CH2:25][CH2:24]1.Cl.CN(C)[CH2:40][CH2:41][CH2:42]N=C=NCC.N1(C2N=C(CC([O-])=O)NC(=O)C=2)CCOCC1.[Na+]>CN(C)C=O>[N:15]1([C:11]2[N:10]=[C:9]([CH2:21][C:22](=[O:36])[N:23]3[C:31]4[C:26](=[C:27]([CH:3]5[CH2:4][CH2:5][CH2:6][N:1]([CH2:40][CH2:41][CH3:42])[CH2:2]5)[CH:28]=[CH:29][CH:30]=4)[CH2:25][CH2:24]3)[NH:8][C:13](=[O:14])[CH:12]=2)[CH2:16][CH2:17][O:18][CH2:19][CH2:20]1
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Komponenten

6

Edukt 4

HCID 1049PyridineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 573895513-methyl-6-(morpholin-4-yl)-2-{2-oxo-2-[4-(trifluoromethyl)-2,3-dihydro-1H-indol-1-yl]ethyl}pyrimidin-4(3H)-oneHCID 136041844Sodium (4-morpholin-4-yl-6-oxo-1,6-dihydropyrimidin-2-yl)acetate

Produkt 1

HCID 136069607
6-(morpholin-4-yl)-2-{2-oxo-2-[4-(1-propylpiperidin-3-yl)-2,3-dihydro-1H-indol-1-yl]ethyl}pyrimidin-4(3H)-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

0.2 ml of pyridine, 25.7 mg of 4-(1-propylpiperidin-3-yl)-2,3-dihydro-1H-indole (reference example 4d) and 17.8 mg of N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride are successively added to a solution of 20.5 mg of sodium [4-(morpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]acetate (example 1d, step 2d) in 0.8 ml of N,N-dimethylformamide. The reaction mixture is stirred at ambient temperature for 24 hours, and then concentrated under reduced pressure. The residue is taken up in 10 ml of water and then extracted with dichloromethane (4×20 ml). The organic phases are combined and then washed with water and concentrated under reduced pressure. After oven-drying, 16.1 mg of 6-(morpholin-4-yl)-2-{2-oxo-2-[4-(1-propylpiperidin-3-yl)-2,3-dihydro-1H-indol-1-yl]ethyl}pyrimidin-4(3H)-one are obtained in the form of a pink solid, the characteristics of which are the following:

Aufarbeitung

  1. concentrationconcentrated under reduced pressure
  2. extractionextracted with dichloromethane (4×20 ml)
  3. washwashed with water
  4. concentrationconcentrated under reduced pressure
  5. customAfter oven-drying

Quellen und Nachweise

ORD-Eintrag
ord-8d04c01b63fa452b91cc7a9647e1e84c
Quelldatensatz
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09133168B2

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