Acetic Anhydride → [2-(N-Methyl-acetamido)-quinazolin-4-yl]-(4-dimethylaminophenyl)-methylamine

HRID 2381011Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2381011
[CH3:1][NH:2][C:3]1[N:12]=[C:11]([N:13]([C:15]2[CH:20]=[CH:19][C:18]([N:21]([CH3:23])[CH3:22])=[CH:17][CH:16]=2)[CH3:14])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1.C(N(CC)CC)C.CN(C1C=CC=CN=1)C.[C:40](OC(=O)C)(=[O:42])[CH3:41]>C(Cl)Cl.C(OCC)(=O)C>[CH3:1][N:2]([C:3]1[N:12]=[C:11]([N:13]([C:15]2[CH:16]=[CH:17][C:18]([N:21]([CH3:22])[CH3:23])=[CH:19][CH:20]=2)[CH3:14])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1)[C:40](=[O:42])[CH3:41]

Komponenten

7

Edukt 4

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 11638105(2-Methylamino-quinazolin-4-yl)-(4-dimethylaminophenyl)-methylamine

Produkt 1

HCID 11710027[2-(N-Methyl-acetamido)-quinazolin-4-yl]-(4-dimethylaminophenyl)-methylamineAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of (2-methylamino-quinazolin-4-yl)-(4-dimethylaminophenyl)-methylamine (40 mg, 0.13 mmol) in 4 mL of methylenechloride cooled at 0° C. was added triethylamine (50 uL, 0.36 mmol), few crystals of dimethylaminopyridine and acetic anhydride (50 uL, 0.53 mmol). The reaction mixture was stirred for 1 h at 0° C., warmed to room temperature, and stirred overnight. The reaction mixture was diluted with 25 mL of ethyl acetate and washed with 25 mL of saturated sodium bicarbonate. The organic layer was dried over anhydrous NaSO4, filtered and concentrated. The residue was purified by chromatography (40% ethyl acetate/hexane) to give the title compound (39 mg, 0.11 mmol, 85%). 1H NMR (CDCl3): 7.65-7.69 (m, 1H), 7.52 (ddd, J=8.4, 6.6, 1.8, 1H), 6.93-7.12 (m, 4H), 6.72 (m, 2H), 3.56 (s, 3H), 3.01 (s, 6H), 2.52 (s, 3H).

Aufarbeitung

  1. temperaturewarmed to room temperature
  2. stirringstirred overnight
  3. washwashed with 25 mL of saturated sodium bicarbonate
  4. dry with materialThe organic layer was dried over anhydrous NaSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by chromatography (40% ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-61393c24458e4eb89aab7f3cd39e15e1
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08258145B2

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