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
Reaction equation
[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]=1Participants
3
Procedure
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)+.
Sources & evidence
- ORD record
- ord-0065ebb8678f48f4af750c1610f42fe1
- Source dataset
- uspto-grants-2014_03
- Patent number
- US08669249B2
Reaction notes
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