4-(Piperazin-1-yl)benzonitrile → 4-(4-((8-Cyclopropyl-2-methyl-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)methyl)piperazin-1-yl)benzonitrile

HRID 1184483Notes

Reaction equation

HRID 1184483 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.[N:18]1([C:24]2[CH:31]=[CH:30][C:27]([C:28]#[N:29])=[CH:26][CH:25]=2)[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]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:21]3[CH2:20][CH2:19][N:18]([C:24]4[CH:25]=[CH:26][C:27]([C:28]#[N:29])=[CH:30][CH:31]=4)[CH2:23][CH2:22]3)[CH:5]=2)[CH2:2][CH2:3]1

Participants

3

Reactant 2

HCID 27339954-(Piperazin-1-yl)benzonitrileHCID 86664220HCID 86664220, compound

Product 1

HCID 667167914-(4-((8-Cyclopropyl-2-methyl-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)methyl)piperazin-1-yl)benzonitrile

Procedure

Using 346A and 4-(piperazin-1-yl)benzonitrile in the general procedure for reductive aminations, the title compound was obtained as a white solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 0.58-0.71 (m, 2H) 0.85-0.96 (m, 2H) 1.42 (d, J=6.82 Hz, 3H) 2.05-2.12 (m, 1H) 2.38-2.48 (m, 4H) 3.27-3.32 (m, 4H) 3.36 (s, 2H) 4.64 (q, J=6.74 Hz, 1H) 6.41 (d, J=1.52 Hz, 1H) 6.68 (d, J=1.77 Hz, 1H) 7.00 (m, J=9.09 Hz, 2H) 7.57 (m, 2H) 10.56 (br. s., 1H). ESI-MS: m/z 403.4 (M+H)+. mp=194.3-195.5° C.

Sources & evidence

ORD record
ord-2b950c7527934eed8ecce726ed85f82d
Source dataset
uspto-grants-2014_03
Patent number
US08669249B2

Reaction notes

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