Dimethylacetoacetamide → 3-[({4-[(3-Chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}methyl)(ethyl)amino]-1-[3-(dimethylamino)-1-methyl-3-oxopropyl]azetidine-3-carboxamide

HRID 1867745

Reaktionsgleichung

Reaktionsgleichung von HRID 1867745
Cl.[Cl:2][C:3]1[C:4]([F:33])=[C:5]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][C:16]([O:31][CH3:32])=[C:17]([CH2:20][N:21]([CH2:29][CH3:30])[C:22]4([C:26]([NH2:28])=[O:27])[CH2:25][NH:24][CH2:23]4)[CH:18]=3)[N:13]=[CH:12][N:11]=2)[CH:6]=[CH:7][CH:8]=1.[CH3:34][N:35]([CH3:42])[C:36](=[O:41])[CH2:37][C:38]([CH3:40])=O>>[Cl:2][C:3]1[C:4]([F:33])=[C:5]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][C:16]([O:31][CH3:32])=[C:17]([CH2:20][N:21]([CH2:29][CH3:30])[C:22]4([C:26]([NH2:28])=[O:27])[CH2:25][N:24]([CH:38]([CH3:40])[CH2:37][C:36]([N:35]([CH3:42])[CH3:34])=[O:41])[CH2:23]4)[CH:18]=3)[N:13]=[CH:12][N:11]=2)[CH:6]=[CH:7][CH:8]=1

Komponenten

3

Edukt 2

HCID 16278DimethylacetoacetamideHCID 690472513-[({4-[(3-Chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}methyl)(ethyl)amino]azetidine-3-carboxamide hydrochloride salt

Produkt 1

HCID 579798953-[({4-[(3-Chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}methyl)(ethyl)amino]-1-[3-(dimethylamino)-1-methyl-3-oxopropyl]azetidine-3-carboxamideAusbeute 50 %

Versuchsvorschrift

3-[({4-[(3-chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}methyl)(ethyl)amino]azetidine-3-carboxamide hydrochloride salt Example 75 was coupled with N,N-dimethylacetoacetamide using the same methodology as for the equivalent step in Example 76 to give the title product (58 mg, 50%) as a white powder; 1H NMR Spectrum: (CDCl3) 1.05 (d, 3H), 2.22 (m, 1H), 2.41 (s, 3H), 2.45 (m, 1H), 2.92 (s, 3H), 2.98 (m, 1H), 3.03 (s, 3H), 3.31 (m, 2H), 3.61 (m, 2H), 3.96 (s, 2H), 3.98 (s, 3H), 5.33 (brs, 1H), 7.17 (m, 2H), 7.24 (s, 1H), 7.51 (brs, 1H), 7.87 (brs, 1H), 7.99 (s, 1H), 8.44 (m, 1H), 8.72 (s, 1H); Mass Spectrum: (M+H)+ 558.

Quellen und Nachweise

ORD-Eintrag
ord-6cb966dabb614491b01b366cd2e6fb0b
Quelldatensatz
uspto-grants-2009_12
Patentnummer
US07632840B2

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