N-ethyl-4-(piperazin-1-yl)benzamide → 4-(4-((8-Benzyl-2-methyl-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)methyl)piperazin-1-yl)-N-ethylbenzamide

HRID 1184487Notes

Reaction equation

HRID 1184487 reaction equation
[CH2:1]([C:8]1[C:13]2[O:14][CH:15]([CH3:19])[C:16](=[O:18])[NH:17][C:12]=2[CH:11]=[C:10]([CH:20]=O)[CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:22]([NH:24][C:25](=[O:38])[C:26]1[CH:31]=[CH:30][C:29]([N:32]2[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]2)=[CH:28][CH:27]=1)[CH3:23]>>[CH2:1]([C:8]1[C:13]2[O:14][CH:15]([CH3:19])[C:16](=[O:18])[NH:17][C:12]=2[CH:11]=[C:10]([CH2:20][N:35]2[CH2:34][CH2:33][N:32]([C:29]3[CH:28]=[CH:27][C:26]([C:25]([NH:24][CH2:22][CH3:23])=[O:38])=[CH:31][CH:30]=3)[CH2:37][CH2:36]2)[CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 28749590N-ethyl-4-(piperazin-1-yl)benzamideHCID 86664223HCID 86664223, compound

Product 1

HCID 667171484-(4-((8-Benzyl-2-methyl-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)methyl)piperazin-1-yl)-N-ethylbenzamide

Procedure

Using 353A and N-ethyl-4-(piperazin-1-yl)benzamide 283 in the general procedure for reductive aminations, the title compound was obtained as a light grey solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 1.09 (t, J=7.20 Hz, 3H) 1.32 (d, J=6.82 Hz, 3H) 2.41-2.49 (m, 4H) 3.16-3.29 (m, 6H) 3.38 (s, 2H) 3.89 (s, 2H) 4.53-4.60 (m, 1H) 6.75-6.82 (m, 2H) 6.93 (m, 2H) 7.14-7.19 (m, 1H) 7.19-7.23 (m, 2 H) 7.24-7.29 (m, 2H) 7.71 (m, 2H) 8.17 (t, J=5.68 Hz, 1H) 10.59 (s, 1H). ESI-MS: m/z 499.4 (M+H)+. mp=198.1-205.7° C.

Sources & evidence

ORD record
ord-d77269a145e547b1949c3c671c27211d
Source dataset
uspto-grants-2014_03
Patent number
US08669249B2

Reaction notes

Loading…