Ethyl Acetate → 5-[4-(6,6-Dimethyl-5,6,7,8-tetrahydroquinazolin-4-yl)-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl]-3-nitropyridin-2-amine

HRID 241225Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 241225
Cl.Cl.[N+:3]([C:6]1[C:7]([NH2:23])=[N:8][CH:9]=[C:10]([C:12]2[CH:13]=[CH:14][C:15]3[O:21][CH2:20][CH2:19][NH:18][CH2:17][C:16]=3[CH:22]=2)[CH:11]=1)([O-:5])=[O:4].Cl[C:25]1[C:34]2[CH2:33][C:32]([CH3:36])([CH3:35])[CH2:31][CH2:30][C:29]=2[N:28]=[CH:27][N:26]=1.C(N(C(C)C)CC)(C)C.C(OCC)(=O)C>CN1CCCC1=O>[CH3:35][C:32]1([CH3:36])[CH2:31][CH2:30][C:29]2[N:28]=[CH:27][N:26]=[C:25]([N:18]3[CH2:17][C:16]4[CH:22]=[C:12]([C:10]5[CH:11]=[C:6]([N+:3]([O-:5])=[O:4])[C:7]([NH2:23])=[N:8][CH:9]=5)[CH:13]=[CH:14][C:15]=4[O:21][CH2:20][CH2:19]3)[C:34]=2[CH2:33]1

Komponenten

6

Edukt 4

HCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 668206213-Nitro-5-(2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl)pyridin-2-amine dihydrochlorideHCID 866478114-Chloro-6,6-dimethyl-5,6,7,8-tetrahydroquinazoline

Produkt 1

HCID 668203605-[4-(6,6-Dimethyl-5,6,7,8-tetrahydroquinazolin-4-yl)-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl]-3-nitropyridin-2-amineAusbeute 81,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Versuchsvorschrift

A solution of 3-nitro-5-(2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl)pyridin-2-amine dihydrochloride (540 mg, 1.50 mmol), 4-chloro-6,6-dimethyl-5,6,7,8-tetrahydroquinazoline (270 mg, 1.37 mmol, reagent preparation 3), and diisopropylethylamine (970 mg, 7.49 mmol) in N-methylpyrrolidinone (3 mL) was stirred at 120° C. for 18 h. After cooling to room temperature ethyl acetate (100 mL) was added, the formed precipitate was filtered off, the organic filtrate was washed with saturated sodium bicarbonate (50 mL), water (2×50 mL), and brine (50 mL), dried over sodium sulfate, filtered and concentrated to afford crude 5-[4-(6,6-dimethyl-5,6,7,8-tetrahydroquinazolin-4-yl)-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl]-3-nitropyridine-2-amine (0.5 g) as a brown solid which was used in the next step without further purification. MS (EI) for C24H26N6O3: 447 (MH+).

Aufarbeitung

  1. additionwas added
  2. filtrationthe formed precipitate was filtered off
  3. washthe organic filtrate was washed with saturated sodium bicarbonate (50 mL), water (2×50 mL), and brine (50 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-63be500c902b4c31a6552d488e01ab8f
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08648066B2

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