Ethylamine → N-ethyl-5-methyl-6-[7-(2-methyl-1H-imidazo[4,5-b]pyridin-6-yl)-2,3-dihydro-1,4-benzoxazepin-4(5H)-yl]pyrimidin-4-amine

HRID 241218Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 241218
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([N:8]2[CH2:14][C:13]3[CH:15]=[C:16]([C:19]4[CH:20]=[C:21]5[NH:27][C:26]([CH3:28])=[N:25][C:22]5=[N:23][CH:24]=4)[CH:17]=[CH:18][C:12]=3[O:11][CH2:10][CH2:9]2)[C:3]=1[CH3:29].[CH2:30]([NH2:32])[CH3:31]>CN1CCCC1=O.C(OCC)(=O)C>[CH2:30]([NH:32][C:2]1[C:3]([CH3:29])=[C:4]([N:8]2[CH2:14][C:13]3[CH:15]=[C:16]([C:19]4[CH:20]=[C:21]5[NH:27][C:26]([CH3:28])=[N:25][C:22]5=[N:23][CH:24]=4)[CH:17]=[CH:18][C:12]=3[O:11][CH2:10][CH2:9]2)[N:5]=[CH:6][N:7]=1)[CH3:31]

Komponenten

5

Edukt 2

HCID 6341EthylamineHCID 595865474-(6-chloro-5-methylpyrimidin-4-yl)-7-(2-methyl-1H-imidazo[4,5-b]pyridin-6-yl)-2,3,4,5-tetrahydro-1,4-benzoxazepine

Produkt 1

HCID 59586184N-ethyl-5-methyl-6-[7-(2-methyl-1H-imidazo[4,5-b]pyridin-6-yl)-2,3-dihydro-1,4-benzoxazepin-4(5H)-yl]pyrimidin-4-amineAusbeute 30 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8857Ethyl AcetateLösungsmittelHCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Versuchsvorschrift

A suspension of 4-(6-chloro-5-methylpyrimidin-4-yl)-7-(2-methyl-1H-imidazo[4,5-b]pyridin-6-yl)-2,3,4,5-tetrahydro-1,4-benzoxazepine (44 mg, 0.11 mmol), and ethylamine (29 mg, 0.65 mmol), in N-methylpyrrolidinone (2 mL) was stirred at 100° C. for 6 h. The reaction mixture was diluted with ethyl acetate (75 mL), washed with saturated sodium bicarbonate (75 mL) and brine (50 mL), and dried over sodium sulfate. Concentration and purification by preparatory HPLC (0.1% aqueous ammonium acetate-acetonitrile) gave N-ethyl-5-methyl-6-[7-(2-methyl-1H-imidazo[4,5-b]pyridin-6-yl)-2,3-dihydro-1,4-benzoxazepin-4(5H)-yl]pyrimidin-4-amine (13 mg, 30% yield) as a white solid. 1H NMR (400 MHz, CD3OD) δ 8.50 (s, 1H), 8.07 (s, 1H), 8.04 (d, 1H), 7.56-7.48 (m, 2H), 7.11 (d, 1H), 4.57 (s, 2H), 4.33 (d, 2H), 3.79 (d, 2H), 3.53-3.39 (q, 2H), 2.64 (s, 3H), 2.04 (s, 3H), 1.21 (t, 3H); MS (EI) for C23H25N7O: 416 (MH+).

Aufarbeitung

  1. washwashed with saturated sodium bicarbonate (75 mL) and brine (50 mL)
  2. dry with materialdried over sodium sulfate
  3. concentrationConcentration and purification by preparatory HPLC (0.1% aqueous ammonium acetate-acetonitrile)

Quellen und Nachweise

ORD-Eintrag
ord-3ac49b21e3c74f479a8afe533058a085
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08648066B2

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