1-Hydroxybenzotriazole → 2,3-Dihydrobenzofuran-7-carboxylic acid methyl-(2-{[3-(1-methyl-2-oxo-1,2-dihydroquinolin-6-yloxy)propyl]pyridin-4-ylmethylamino}ethyl)amide dihydrochloride

HRID 1504181

Reaktionsgleichung

Reaktionsgleichung von HRID 1504181
N=C=N.ON1C2C=CC=CC=2N=N1.[CH3:14][N:15]1[C:24]2[C:19](=[CH:20][C:21]([O:25][CH2:26][CH2:27][CH2:28][N:29]([CH2:37][CH2:38][NH:39][CH3:40])[CH2:30][C:31]3[CH:36]=[CH:35][N:34]=[CH:33][CH:32]=3)=[CH:22][CH:23]=2)[CH:18]=[CH:17][C:16]1=[O:41].[O:42]1[C:46]2[C:47]([C:51](O)=[O:52])=[CH:48][CH:49]=[CH:50][C:45]=2[CH2:44][CH2:43]1.C(OC(=O)C)C.[ClH:60]>C(OCC)(=O)C.C1COCC1.C(#N)C>[ClH:60].[ClH:60].[CH3:40][N:39]([CH2:38][CH2:37][N:29]([CH2:28][CH2:27][CH2:26][O:25][C:21]1[CH:20]=[C:19]2[C:24](=[CH:23][CH:22]=1)[N:15]([CH3:14])[C:16](=[O:41])[CH:17]=[CH:18]2)[CH2:30][C:31]1[CH:36]=[CH:35][N:34]=[CH:33][CH:32]=1)[C:51]([C:47]1[C:46]2[O:42][CH2:43][CH2:44][C:45]=2[CH:50]=[CH:49][CH:48]=1)=[O:52]

Komponenten

9

Edukt 5

HCID 757711-HydroxybenzotriazoleHCID 160435CarbodiimideHCID 27950142,3-Dihydro-1-benzofuran-7-carboxylic acidHCID 21866389Hydrogen chloride-ethyl acetateHCID 669605791-Methyl-6-{3-[(2-methylamino-ethyl)-pyridin-4-ylmethyl-amino]-propoxy}-1H-quinolin-2-one

Produkt 1

HCID 706571802,3-Dihydrobenzofuran-7-carboxylic acid methyl-(2-{[3-(1-methyl-2-oxo-1,2-dihydroquinolin-6-yloxy)propyl]pyridin-4-ylmethylamino}ethyl)amide dihydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6342AcetonitrileLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

PS-Carbodiimide resin(1.3 g) and 1-hydroxy benzotriazole (HOBt) (230 mg) were added to acetonitrile and THF solution (4 ml+6 ml) of 1-methyl-6-{3-[(2-methylamino ethyl)pyridin-4-ylmethylamino]propoxy}-1H-quinolin-2-one(304 mg) and 2,3-dihydrobenzofuran-7-carboxylic acid(164 mg). The mixture was stirred at room temperature overnight. After the reaction mixture was filtrated and condensed under reduced pressure, the residue was purified by silica gel column chromatography (ethyl acetate: methanol=1:0→10:1). The purified product was condensed under reduced pressure. A 4N-hydrogen chloride ethyl acetate solution(0.35 ml) was added to an ethyl acetate solution of the residue. The precipitated insoluble matter was separated, washed with ethyl acetate, and dried to give the title compound(324.2 mg) as a white powder.

Aufarbeitung

  1. filtrationAfter the reaction mixture was filtrated
  2. customcondensed under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (ethyl acetate: methanol=1:0→10:1)
  4. customcondensed under reduced pressure
  5. customThe precipitated insoluble matter was separated
  6. washwashed with ethyl acetate
  7. customdried

Quellen und Nachweise

ORD-Eintrag
ord-9158af4bec874db3957a1078403b2886
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09212187B2

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