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

Participants

Role	Name	HCID	Charge
Reactant	N-ethyl-4-(piperazin-1-yl)benzamide	HCID 28749590	—
Reactant	8-Hydroxy-2-methyl-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-6-carbaldehyde	HCID 86664225	—
Product	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	HCID 66717152	—

Reaction Steps

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)+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08669249B2
Source dataset	uspto-grants-2014_03
ORD ID	ord-d5a8b8fa460b4356b1d3737018d74c8a
Source note	uspto-grants-2014_03