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

HRID 2278614
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2278614
N1C=CC=CC=1.[F:7][C:8]([F:19])([F:18])[C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH2:11][CH2:12][NH:13]2.Cl.CN(C)CCCN=C=NCC.[CH3:32][N:33]1[C:38](=[O:39])[CH:37]=[C:36]([N:40]2[CH2:45][CH2:44][O:43][CH2:42][CH2:41]2)[N:35]=[C:34]1[CH2:46][C:47]([O-])=[O:48].[Na+]>CN(C)C=O.C(OCC)(=O)C.O>[CH3:32][N:33]1[C:38](=[O:39])[CH:37]=[C:36]([N:40]2[CH2:45][CH2:44][O:43][CH2:42][CH2:41]2)[N:35]=[C:34]1[CH2:46][C:47](=[O:48])[N:13]1[C:14]2[C:10](=[C:9]([C:8]([F:7])([F:18])[F:19])[CH:17]=[CH:16][CH:15]=2)[CH2:11][CH2:12]1
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Komponenten

8

Edukt 4

HCID 1049PyridineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 162444454-(Trifluoromethyl)indolineHCID 57523684Sodium [1-methyl-4-(morpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]acetate

Produkt 1

HCID 573895513-methyl-6-(morpholin-4-yl)-2-{2-oxo-2-[4-(trifluoromethyl)-2,3-dihydro-1H-indol-1-yl]ethyl}pyrimidin-4(3H)-one
Ausbeute 30,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

3 ml of pyridine, 94 mg of 4-trifluoromethyl-2,3-dihydro-1H-indole and 153 mg of N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride are successively added to a solution of 138 mg of sodium [1-methyl-4-(morpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]acetate in 3 ml of N,N-dimethylformamide. The reaction mixture is stirred at ambient temperature for 16 hours. After the addition of 50 ml of water and extraction with ethyl acetate (3×15 ml), the organic phases are combined and then washed with water (2×15 ml), and a saturated aqueous sodium chloride solution (15 ml), and then dried over magnesium sulfate, filtered through sintered glass, and concentrated under reduced pressure. The solid obtained is washed with diethyl ether (5 ml) and then dried, so as to give 64 mg of 3-methyl-6-(morpholin-4-yl)-2-{2-oxo-2-[4-(trifluoromethyl)-2,3-dihydro-1H-indol-1-yl]ethyl}pyrimidin-4(3H)-one in the form of a pink solid, the characteristics of which are the following:

Aufarbeitung

  1. washwashed with water (2×15 ml)
  2. dry with materiala saturated aqueous sodium chloride solution (15 ml), and then dried over magnesium sulfate
  3. filtrationfiltered through sintered glass
  4. concentrationconcentrated under reduced pressure
  5. customThe solid obtained
  6. washis washed with diethyl ether (5 ml)
  7. customdried

Quellen und Nachweise

ORD-Eintrag
ord-c7d7c19ed6c04fbb8066f0b74fc57d62
Quelldatensatz
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09133168B2

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