Triethylamine → HCID 66893244, Verbindung

HRID 1479680Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1479680
[NH2:1][C:2]1[C:11]2[N:10]=[CH:9][C:8]([CH2:12][CH2:13][C:14]3[CH:22]=[CH:21][C:17]([C:18](Cl)=[O:19])=[CH:16][C:15]=3[CH3:23])=[CH:7][C:6]=2[C:5]2[CH:24]=[CH:25][C:26]([CH3:28])=[CH:27][C:4]=2[N:3]=1.C(N(CC)CC)C.[NH2:36][CH2:37][CH2:38][NH:39][C:40](=[O:42])[CH3:41]>CCOCC.C(OCC)(=O)C.O>[C:40]([NH:39][CH2:38][CH2:37][NH:36][C:18](=[O:19])[C:17]1[CH:21]=[CH:22][C:14]([CH2:13][CH2:12][C:8]2[CH:9]=[N:10][C:11]3[C:2]([NH2:1])=[N:3][C:4]4[CH:27]=[C:26]([CH3:28])[CH:25]=[CH:24][C:5]=4[C:6]=3[CH:7]=2)=[C:15]([CH3:23])[CH:16]=1)(=[O:42])[CH3:41]

Komponenten

7

Edukt 3

HCID 8471TriethylamineHCID 66082N-(2-aminoethyl)acetamideHCID 86652358HCID 86652358, Verbindung

Produkt 1

HCID 66893244HCID 66893244, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 4-(2-(5-amino-8-methylbenzo[f][1,7]naphthyridin-2-yl)ethyl)-3-methylbenzoyl chloride (Example 116/Step 2) and triethylamine (2.5 eq.) in ether (0.05 M) was added N-(2-aminoethyl)acetamide (5.0 eq.). The reaction mixture was stirred for overnight. Then the reaction mixture was diluted with ethyl acetate and water. The two phases were separated, and the aqueous layer was extracted twice with ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous MgSO4, and concentrated en vaccuo. The crude material was purified by flash chromatography on a COMBIFLASH® system (ISCO) using 0-80% ethyl acetate in hexane to give N-(2-acetamidoethyl)-4-(2-(5-amino-8-methylbenzo[f][1,7]naphthyridin-2-yl)ethyl)-3-methylbenzamide as a white solid. 1H NMR (CDCl3): δ 8.61 (s, 1H), 8.38 (s, 1H), 8.07 (d, 1H), 7.65 (s, 1H), 7.51-7.56 (m, 2H), 7.10-7.16 (m, 2H), 6.25 (br, 2H), 3.50-3.59 (m, 4H), 3.08-3.16 (m, 4H), 2.62 (s, 3H), 2.52 (s, 3H), 2.35 (s, 3H). LRMS [M+H]=455.2.

Aufarbeitung

  1. customThe two phases were separated
  2. extractionthe aqueous layer was extracted twice with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over anhydrous MgSO4
  5. concentrationconcentrated en vaccuo
  6. customThe crude material was purified by flash chromatography on a COMBIFLASH® system (ISCO)

Quellen und Nachweise

ORD-Eintrag
ord-55b62b9056ed4c93a13cfa01640cb75b
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09408907B2

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