1,4-Dioxane hydrochloride → 3-[({4-[(3-chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}methyl)(methyl)amino]-N-methylazetidine-3-carboxamide

HRID 1867768Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1867768
Cl.O1CCOCC1.[Cl:8][C:9]1[C:10]([F:46])=[C:11]([NH:15][C:16]2[C:25]3[C:20](=[CH:21][C:22]([O:44][CH3:45])=[C:23]([CH2:26][N:27]([CH3:43])[C:28]4([C:39]([NH:41][CH3:42])=[O:40])[CH2:31][N:30](C(OC(C)(C)C)=O)[CH2:29]4)[CH:24]=3)[N:19]=[CH:18][N:17]=2)[CH:12]=[CH:13][CH:14]=1>O1CCOCC1>[Cl:8][C:9]1[C:10]([F:46])=[C:11]([NH:15][C:16]2[C:25]3[C:20](=[CH:21][C:22]([O:44][CH3:45])=[C:23]([CH2:26][N:27]([CH3:43])[C:28]4([C:39]([NH:41][CH3:42])=[O:40])[CH2:31][NH:30][CH2:29]4)[CH:24]=3)[N:19]=[CH:18][N:17]=2)[CH:12]=[CH:13][CH:14]=1

Komponenten

4

Edukt 2

HCID 204431481,4-Dioxane hydrochlorideHCID 69047412Tert-butyl 3-[({4-[(3-chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}methyl) (methyl)amino]-3-[(methylamino)carbonyl]azetidine-1-carboxylate

Produkt 1

HCID 579798733-[({4-[(3-chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}methyl)(methyl)amino]-N-methylazetidine-3-carboxamideAusbeute 130,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A solution of HCl/1,4-dioxan (1/5) (2 ml) was added dropwise to a solution of tert-butyl 3-[({4-[(3-chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}methyl)(methyl)amino]-3-[(methylamino)carbonyl]azetidine-1-carboxylate (310 mg, 0.56 mmol) in 1,4-dioxan (6 ml). The reaction mixture was stirred overnight, then concentrated under reduced pressure. Three triturations in methanol/dichloromethane/diethyl ether afforded the isolation of a hydrochloride salt of 3-[({4-[(3-chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}methyl)(methyl)amino]-N-methylazetidine-3-carboxamide as a solid (336 mg, 100%). 1H NMR Spectrum: (DMSO d6) 2.16 (s, 3H), 2.71 (d, 3H), 3.70 (s, 2H), 3.97 (m, 2H), 4.03 (s, 3H), 4.13 (m, 2H), 7.37 (m, 2H), 7.55 (t, 1H), 7.66 (t, 1H), 8.31 (brs, 1H), 8.90 (brs, 2H), 9.27 (s, 1H), 9.75 (brs, 1H); Mass Spectrum: (M+H)+ 459.

Aufarbeitung

  1. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-f667a2f97c2148fcb5a4df04b6a5b70c
Quelldatensatz
uspto-grants-2009_12
Patentnummer
US07632840B2

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