Triethylamine → 4-(Chloromethyl)-N-(4-methyl-3-((4-(3-pyridinyl)-2-pyrimidinyl)amino)phenyl)benzamide

HRID 736295

Reaktionsgleichung

Reaktionsgleichung von HRID 736295
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:21])=[C:6]([NH:8][C:9]2[N:14]=[C:13]([C:15]3[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=3)[CH:12]=[CH:11][N:10]=2)[CH:7]=1.C(N(CC)CC)C.[Cl:29][CH2:30][C:31]1[CH:39]=[CH:38][C:34]([C:35](Cl)=[O:36])=[CH:33][CH:32]=1>O1CCCC1>[Cl:29][CH2:30][C:31]1[CH:39]=[CH:38][C:34]([C:35]([NH:1][C:2]2[CH:3]=[CH:4][C:5]([CH3:21])=[C:6]([NH:8][C:9]3[N:14]=[C:13]([C:15]4[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=4)[CH:12]=[CH:11][N:10]=3)[CH:7]=2)=[O:36])=[CH:33][CH:32]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 701364-(Chloromethyl)benzoyl chlorideHCID 9965429Imatinib amine

Produkt 1

HCID 101810754-(Chloromethyl)-N-(4-methyl-3-((4-(3-pyridinyl)-2-pyrimidinyl)amino)phenyl)benzamideAusbeute 87,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

N-(5-amino-2-methylphenyl)-4-(3-pyridyl)-2-pyrimidine-amine (2.83 g, 8.29 mmol) was dissolved in tetrahydrofuran (20 ml), triethylamine (1.4 ml, 9.95 mmol) was added thereto, and the mixture was stirred for 30 minutes. 4-Chloromethyl benzoyl chloride (2.03 g, 10.78 mmol) was added and the whole mixture was reacted under reflux for 4 hours. The mixture was filtered, and the filtrate was concentrated and crystallized from water to give N-(5-(4-chloromethylbenzoylamino)-2-methylphenyl)-4-(3-pyridyl)-2-pyrimidine-amine (3.12 g).

Aufarbeitung

  1. customthe whole mixture was reacted
  2. temperatureunder reflux for 4 hours
  3. filtrationThe mixture was filtered
  4. concentrationthe filtrate was concentrated
  5. customcrystallized from water

Quellen und Nachweise

ORD-Eintrag
ord-c3f9a4b5ff05412180b2d92b442d526f
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07595323B2

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