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

HRID 1184495Notes

Reaction equation

HRID 1184495 reaction equation
[OH:1][C:2]1[C:7]2[O:8][CH:9]([CH3:13])[C:10](=[O:12])[NH:11][C:6]=2[CH:5]=[C:4]([CH:14]=O)[CH:3]=1.[CH2:16]([NH:18][C:19](=[O:32])[C:20]1[CH:25]=[CH:24][C:23]([N:26]2[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)=[CH:22][CH:21]=1)[CH3:17]>>[CH2:16]([NH:18][C:19](=[O:32])[C:20]1[CH:21]=[CH:22][C:23]([N:26]2[CH2:27][CH2:28][N:29]([CH2:14][C:4]3[CH:3]=[C:2]([OH:1])[C:7]4[O:8][CH:9]([CH3:13])[C:10](=[O:12])[NH:11][C:6]=4[CH:5]=3)[CH2:30][CH2:31]2)=[CH:24][CH:25]=1)[CH3:17]

Participants

3

Reactant 2

HCID 28749590N-ethyl-4-(piperazin-1-yl)benzamideHCID 866642258-Hydroxy-2-methyl-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-6-carbaldehyde

Product 1

HCID 66717152N-Ethyl-4-(4-((8-hydroxy-2-methyl-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)methyl)piperazin-1-yl)benzamide

Procedure

Using 359A 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 1.03 (t, J=7.07 Hz, 3H) 1.37 (d, J=6.82 Hz, 3H) 2.90-3.13 (m, 4H) 3.13-3.24 (m, 2H) 3.33 (br. s., 2H) 3.92 (d, J=12.63 Hz, 2H) 4.16 (br. s., 2H) 4.57 (q, J=6.65 Hz, 1H) 6.43 (d, J=1.77 Hz, 1H) 6.57 (d, J=1.52 Hz, 1H) 6.94 (d, J=8.84 Hz, 2H) 7.70 (d, J=8.84 Hz, 2H) 8.18 (t, J=5.43 Hz, 1H) 9.66 (d, J=9.35 Hz, 1H) 10.75 (s, 1H). ESI-MS: m/z 425.4 (M+H)+.

Sources & evidence

ORD record
ord-d5a8b8fa460b4356b1d3737018d74c8a
Source dataset
uspto-grants-2014_03
Patent number
US08669249B2

Reaction notes

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