Methylamine hydrochloride → N-Methyl-4-(4-((2-methyl-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)methyl)piperidin-1-yl)benzamide

HRID 1184503Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1184503
[CH3:1][CH:2]1[O:7][C:6]2[CH:8]=[CH:9][C:10]([CH2:12][CH:13]3[CH2:18][CH2:17][N:16]([C:19]4[CH:29]=[CH:28][C:22]([C:23](OCC)=[O:24])=[CH:21][CH:20]=4)[CH2:15][CH2:14]3)=[CH:11][C:5]=2[NH:4][C:3]1=[O:30].Cl.[CH3:32][NH2:33]>>[CH3:32][NH:33][C:23](=[O:24])[C:22]1[CH:28]=[CH:29][C:19]([N:16]2[CH2:15][CH2:14][CH:13]([CH2:12][C:10]3[CH:9]=[CH:8][C:6]4[O:7][CH:2]([CH3:1])[C:3](=[O:30])[NH:4][C:5]=4[CH:11]=3)[CH2:18][CH2:17]2)=[CH:20][CH:21]=1

Komponenten

3

Edukt 2

HCID 6364545Methylamine hydrochlorideHCID 67283662Ethyl 4-(4-((2-methyl-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)methyl)piperidin-1-yl)benzoate

Produkt 1

HCID 66716958N-Methyl-4-(4-((2-methyl-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)methyl)piperidin-1-yl)benzamide

Versuchsvorschrift

Saponification of 390D was performed using the general procedure for hydrolysis of carboxylic esters. The resulting carboxylic acid and methylamine hydrochloride were used in the general procedure for coupling an amine to a carboxylic acid to give the title compound as a pinkish, tan solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.13-1.28 (m, 2H) 1.40 (d, J=6.57 Hz, 3H) 1.55-1.71 (m, 3H) 2.44 (d, J=6.57 Hz, 2H) 2.62-2.78 (m, 5H) 3.82 (d, J=12.63 Hz, 2H) 4.61 (q, J=6.65 Hz, 1H) 6.65-6.77 (m, 2H) 6.82-6.95 (m, 3H) 7.67 (d, J=9.09 Hz, 2H) 8.05-8.15 (m, 1H) 10.59 (s, 1H). ESI-MS: m/z 394.3 (M+H)+.

Quellen und Nachweise

ORD-Eintrag
ord-0065ebb8678f48f4af750c1610f42fe1
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08669249B2

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