N-methyl-4-(piperazin-1-yl)benzamide → HCID 66716999, compound

HRID 1184514Notes

Reaction equation

HRID 1184514 reaction equation
[CH2:1]([O:3][C:4]1[C:9]2[O:10][CH:11]([CH3:15])[C:12](=[O:14])[NH:13][C:8]=2[CH:7]=[C:6]([CH:16]=O)[CH:5]=1)[CH3:2].[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>>[CH2:1]([O:3][C:4]1[C:9]2[O:10][CH:11]([CH3:15])[C:12](=[O:14])[NH:13][C:8]=2[CH:7]=[C:6]([CH2:16][N:30]2[CH2:29][CH2:28][N:27]([C:24]3[CH:23]=[CH:22][C:21]([C:20]([NH:19][CH3:18])=[O:33])=[CH:26][CH:25]=3)[CH2:32][CH2:31]2)[CH:5]=1)[CH3:2]

Participants

3

Reactant 2

HCID 28749530N-methyl-4-(piperazin-1-yl)benzamideHCID 718134828-Ethoxy-2-methyl-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-6-carbaldehyde

Product 1

HCID 66716999HCID 66716999, compound

Procedure

Using 398B 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 1.32 (t, J=7.07 Hz, 3H) 1.37-1.44 (m, 3H) 2.41-2.49 (m, 4H) 2.74 (d, J=4.55 Hz, 3H) 3.24 (d, J=5.05 Hz, 4H) 3.40 (s, 2H) 3.98-4.12 (m, 2H) 4.55-4.65 (m, 1H) 6.51 (d, J=1.77 Hz, 1 H) 6.63 (d, J=1.77 Hz, 1H) 6.94 (d, J=8.84 Hz, 2H) 7.70 (d, J=8.84 Hz, 2H) 8.14 (q, J=4.72 Hz, 1H) 10.57 (s, 1H). ESI-MS: m/z 439.4 (M+H)+. mp 228.2-233.0° C.

Sources & evidence

ORD record
ord-482f5f56d8bf40aa8e1c5fe297e53ad5
Source dataset
uspto-grants-2014_03
Patent number
US08669249B2

Reaction notes

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