N-ethyl-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-ethylbenzamide

HRID 1184521Notes

Reaction equation

HRID 1184521 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.[CH2:19]([NH:21][C:22](=[O:35])[C:23]1[CH:28]=[CH:27][C:26]([N:29]2[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]2)=[CH:25][CH:24]=1)[CH3:20]>>[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:32]2[CH2:31][CH2:30][N:29]([C:26]3[CH:25]=[CH:24][C:23]([C:22]([NH:21][CH2:19][CH3:20])=[O:35])=[CH:28][CH:27]=3)[CH2:34][CH2:33]2)[CH:5]=1

Participants

3

Reactant 2

HCID 28749590N-ethyl-4-(piperazin-1-yl)benzamideHCID 86664227HCID 86664227, compound

Product 1

HCID 667168354-(4-((8-(Difluoromethoxy)-2-methyl-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)methyl)piperazin-1-yl)-N-ethylbenzamide

Procedure

Using 403A and N-ethyl-4-(piperazin-1-yl)benzamide 283 in the general procedure for reductive aminations, the title compound was obtained as a white solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 1.09 (t, J=7.20 Hz, 3H) 1.43 (d, J=6.82 Hz, 3H) 2.46-2.49 (m, 4H) 3.19-3.29 (m, 6H) 3.43 (s, 2H) 4.70-4.77 (m, 1H) 6.80 (s, 2H) 6.93 (d, J=8.84 Hz, 2H) 6.95-7.34 (m, 1H) 7.71 (d, J=9.09 Hz, 2H) 8.17 (t, J=5.56 Hz, 1H) 10.80 (s, 1H). ESI-MS: m/z 475.4 (M+H)+. mp 219.3-223.8° C.

Sources & evidence

ORD record
ord-5f1388c5a2974da39cbb4fe31c476e51
Source dataset
uspto-grants-2014_03
Patent number
US08669249B2

Reaction notes

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