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

HRID 1184476Notes

Reaction equation

HRID 1184476 reaction equation
[CH:1]1([C:4]2[C:9]3[O:10][CH:11]([CH3:15])[C:12](=[O:14])[NH:13][C:8]=3[CH:7]=[C:6]([CH:16]=O)[CH:5]=2)[CH2:3][CH2:2]1.[CH2:18]([NH:20][C:21](=[O:34])[C:22]1[CH:27]=[CH:26][C:25]([N:28]2[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]2)=[CH:24][CH:23]=1)[CH3:19]>>[CH:1]1([C:4]2[C:9]3[O:10][CH:11]([CH3:15])[C:12](=[O:14])[NH:13][C:8]=3[CH:7]=[C:6]([CH2:16][N:31]3[CH2:30][CH2:29][N:28]([C:25]4[CH:24]=[CH:23][C:22]([C:21]([NH:20][CH2:18][CH3:19])=[O:34])=[CH:27][CH:26]=4)[CH2:33][CH2:32]3)[CH:5]=2)[CH2:2][CH2:3]1

Participants

3

Reactant 2

HCID 28749590N-ethyl-4-(piperazin-1-yl)benzamideHCID 86664220HCID 86664220, compound

Product 1

HCID 667168604-(4-((8-Cyclopropyl-2-methyl-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)methyl)piperazin-1-yl)-N-ethylbenzamide

Procedure

Using 346A and N-ethyl-4-(piperazin-1-yl)benzamide 283 in the general procedure for reductive aminations, the title compound was obtained as an off-white solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 0.60-0.70 (m, 2H) 0.88-0.94 (m, 2H) 1.09 (t, J=7.07 Hz, 3H) 1.43 (d, J=6.57 Hz, 3H) 2.04-2.12 (m, 1H) 2.41-2.49 (m, 4H) 3.17-3.29 (m, 6H) 3.36 (s, 2H) 4.64 (q, J=6.82 Hz, 1H) 6.41 (d, J=1.52 Hz, 1H) 6.69 (d, J=1.77 Hz, 1H) 6.92 (m, J=9.09 Hz, 2H) 7.71 (m, J=8.84 Hz, 2H) 8.17 (t, J=5.56 Hz, 1H) 10.55 (s, 1H). ESI-MS: m/z 449.4 (M+H)+.

Sources & evidence

ORD record
ord-18c3b8fbac734d2e9f1355d6a3bfb450
Source dataset
uspto-grants-2014_03
Patent number
US08669249B2

Reaction notes

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