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

HRID 1184523Notes

Reaction equation

HRID 1184523 reaction equation
[F:1][CH:2]([F:18])[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.[CH3:19][NH:20][C:21](=[O:35])[C:22]1[CH:27]=[CH:26][C:25]([N:28]2[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]2)=[C:24]([CH3:34])[CH:23]=1>>[F:1][CH:2]([F:18])[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:31]2[CH2:30][CH2:29][N:28]([C:25]3[CH:26]=[CH:27][C:22]([C:21]([NH:20][CH3:19])=[O:35])=[CH:23][C:24]=3[CH3:34])[CH2:33][CH2:32]2)[CH:5]=1

Participants

3

Reactant 2

HCID 287495403,N-Dimethyl-4-piperazin-1-yl-benzamideHCID 86664227HCID 86664227, compound

Product 1

HCID 667170894-(4-((8-(Difluoromethoxy)-2-methyl-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)methyl)piperazin-1-yl)-N,3-dimethylbenzamide

Procedure

Using 403A and N,3-dimethyl-4-(piperazin-1-yl)benzamide 298 in the general procedure for reductive aminations, the title compound was obtained as a white solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 1.36-1.49 (m, 3H) 2.26 (s, 3H) 2.52-2.62 (m, 4H) 2.74 (d, J=4.55 Hz, 3H) 2.89 (br. s., 4H) 3.41-3.50 (m, 2H) 4.74 (q, J=6.65 Hz, 1H) 6.81 (s, 2H) 6.92-7.37 (m, 2H) 7.56-7.66 (m, 2H) 8.23 (d, J=4.55 Hz, 1H) 10.81 (s, 1H). ESI-MS: m/z 475.4 (M+H)+.

Sources & evidence

ORD record
ord-ab2c54e58b324dfd805b84a7e4a45e96
Source dataset
uspto-grants-2014_03
Patent number
US08669249B2

Reaction notes

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