Acetyl chloride → 1-{2-[3-Methoxy-4-(4-methyl-imidazol-1-yl)-phenylamino]-8-phenyl-7,8-dihydro-5H-pyrido[4,3-d]pyrimidin-6-yl}-ethanone

HRID 2076039Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2076039
Cl.[CH3:2][O:3][C:4]1[CH:5]=[C:6]([NH:16][C:17]2[N:18]=[CH:19][C:20]3[CH2:26][NH:25][CH2:24][CH:23]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[C:21]=3[N:22]=2)[CH:7]=[CH:8][C:9]=1[N:10]1[CH:14]=[C:13]([CH3:15])[N:12]=[CH:11]1.C(N(C(C)C)CC)(C)C.[C:42](Cl)(=[O:44])[CH3:43]>C(Cl)Cl>[CH3:2][O:3][C:4]1[CH:5]=[C:6]([NH:16][C:17]2[N:18]=[CH:19][C:20]3[CH2:26][N:25]([C:42](=[O:44])[CH3:43])[CH2:24][CH:23]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[C:21]=3[N:22]=2)[CH:7]=[CH:8][C:9]=1[N:10]1[CH:14]=[C:13]([CH3:15])[N:12]=[CH:11]1

Komponenten

5

Edukt 3

HCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 44194157[3-Methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-(8-phenyl-5,6,7,8-tetrahydro-pyrido[4,3-d]pyrimidin-2-yl)-amine hydrochloride

Produkt 1

HCID 441941591-{2-[3-Methoxy-4-(4-methyl-imidazol-1-yl)-phenylamino]-8-phenyl-7,8-dihydro-5H-pyrido[4,3-d]pyrimidin-6-yl}-ethanoneAusbeute 30 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a suspension of [3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-(8-phenyl-5,6,7,8-tetrahydro-pyrido[4,3-d]pyrimidin-2-yl)-amine hydrochloride (65 mg, 0.15 mmol) in methylen chloride (2 mL) was added at room temperature NN,-diisopropyl ethyl amine (28 mg, 0.22 mmol) and after 2 minutes acetyl chloride (12.5 mg, 0.16 mmol). The reaction was stirred at room temperature over night. The solvent was evaporated under reduced pressure and the residue was purified by column chromatography on silica gel using dichloromethane/methanol (19:1 v/v) as eluent to yield the title compound (20 mg, 30%) as a yellow gum. MS ISP (m/e): 455.3 (100) [(M+H)+]. 1H NMR (CDCl3, 300 MHz): δ (ppm)=8.38 (s, 1H), 7.61 (s, 1H), 7.56 (s, 1H), 7.20-7.33 (m, 3H), 7.05-7.08 (m, 3H), 6.81 (s, 1H), 6.79 (d, 1H), 5.18 (d, 1H), 4.46 (d, 1H), 4.21 (t, 1H), 3.90 (m, 2H), 3.46 (s, 3H), 2.27 (s, 3H), 1.71 (s, 3H).

Aufarbeitung

  1. additionwas added at room temperature NN
  2. customThe solvent was evaporated under reduced pressure
  3. customthe residue was purified by column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-c567f903cb5d4dedadb399e514eba486
Quelldatensatz
uspto-grants-2011_04
Patentnummer
US07923450B2

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