N-methyl-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-methylbenzamide

HRID 1184477Notes

Reaction equation

HRID 1184477 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.[CH3:18][NH:19][C:20](=[O:33])[C:21]1[CH:26]=[CH:25][C:24]([N:27]2[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]2)=[CH:23][CH:22]=1>>[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:30]3[CH2:29][CH2:28][N:27]([C:24]4[CH:23]=[CH:22][C:21]([C:20]([NH:19][CH3:18])=[O:33])=[CH:26][CH:25]=4)[CH2:32][CH2:31]3)[CH:5]=2)[CH2:2][CH2:3]1

Participants

3

Reactant 2

HCID 28749530N-methyl-4-(piperazin-1-yl)benzamideHCID 86664220HCID 86664220, compound

Product 1

HCID 667169704-(4-((8-Cyclopropyl-2-methyl-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)methyl)piperazin-1-yl)-N-methylbenzamide

Procedure

Using 346A and N-methyl-4-(piperazin-1-yl)benzamide 282 in the general procedure for reductive aminations, the title compound was obtained as a white solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 0.60-0.71 (m, 2H) 0.87-0.95 (m, 2H) 1.43 (d, J=6.82 Hz, 3H) 2.04-2.12 (m, 1H) 2.40-2.48 (m, 4 H) 2.73 (d, J=4.55 Hz, 3H) 3.18-3.26 (m, 4H) 3.36 (s, 2H) 4.61-4.67 (m, 1H) 6.41 (d, J=1.77 Hz, 1H) 6.69 (d, J=1.77 Hz, 1H) 6.93 (m, 2H) 7.69 (m, 2H) 8.14 (q, J=4.21 Hz, 1H) 10.55 (s, 1H). ESI-MS: m/z 435.4 (M+H)+. mp=256.1-258.6° C.

Sources & evidence

ORD record
ord-3af6dc5d7a7941c3ab23b697fa9a299f
Source dataset
uspto-grants-2014_03
Patent number
US08669249B2

Reaction notes

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