N-methyl-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-methylbenzamide

HRID 1184520Notes

Reaction equation

HRID 1184520 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:34])[C:22]1[CH:27]=[CH:26][C:25]([N:28]2[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]2)=[CH:24][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:24]=[CH:23][C:22]([C:21]([NH:20][CH3:19])=[O:34])=[CH:27][CH:26]=3)[CH2:33][CH2:32]2)[CH:5]=1

Participants

3

Reactant 2

HCID 28749530N-methyl-4-(piperazin-1-yl)benzamideHCID 86664227HCID 86664227, compound

Product 1

HCID 667173044-(4-((8-(Difluoromethoxy)-2-methyl-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)methyl)piperazin-1-yl)-N-methylbenzamide

Procedure

Using 403A 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 1.43 (d, J=6.82 Hz, 3H) 2.45-2.49 (m, 4H) 2.73 (d, J=4.55 Hz, 3H) 3.24 (d, J=4.80 Hz, 4H) 3.43 (s, 2H) 4.74 (q, J=6.74 Hz, 1H) 6.80 (s, 2H) 6.93 (d, J=9.09 Hz, 2H) 6.95-7.35 (m, 1H) 7.70 (d, J=8.84 Hz, 2H) 8.10-8.17 (m, 1H) 10.80 (s, 1H). ESI-MS: m/z 461.4 (M+H)+. mp 210.4-213.0° C.

Sources & evidence

ORD record
ord-ef5d6b86c8a941c4a248529ee7eb56c3
Source dataset
uspto-grants-2014_03
Patent number
US08669249B2

Reaction notes

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