Potassium Carbonate → 1-Methyl-4-(4-methyl-3'-nitro-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-6'-yl)-piperazin-2-one

HRID 646933Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][CH:11]([CH3:14])[CH2:10][CH2:9]2)[C:5]([N+:15]([O-:17])=[O:16])=[CH:4][CH:3]=1.Br.[CH3:19][N:20]1[CH2:25][CH2:24][NH:23][CH2:22][C:21]1=[O:26].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:19][N:20]1[CH2:25][CH2:24][N:23]([C:2]2[N:7]=[C:6]([N:8]3[CH2:13][CH2:12][CH:11]([CH3:14])[CH2:10][CH2:9]3)[C:5]([N+:15]([O-:17])=[O:16])=[CH:4][CH:3]=2)[CH2:22][C:21]1=[O:26]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 6′-chloro-4-methyl-3′-nitro-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl (as prepared in Example 55, step (a)) (510 mg, 2.00 mmol) in DMF (10 mL) was added 1-methyl piperazinone hydrobromide (390 mg, 2.00 mmol) and K2CO3 (691 mg, 5.00 mmol). The resulting mixture was heated at 100° C. overnight. DMF was removed in vacuo and the residue obtained was purified on silica (20-100% EtOAc:hexane) to obtain the title compound (540 mg, 81%). 1H-NMR (CDCl3; 400 MHz): δ 8.15 (d, 1H, J=9.1 Hz), 5.94 (d, 1H, J=9.1 Hz), 4.22 (s, 2H), 3.88 (m, 2H), 3.76 (m, 2H), 3.46 (m, 2H), 3.01-2.92 (m, 5H), 1.68 (m, 3H), 1.25 (m, 2H), 0.93 (d, 3H, J=6.3 Hz).

Workup

customDMF was removed in vacuo
customthe residue obtained
customwas purified on silica (20-100% EtOAc:hexane)

Sources & evidence

ORD record: ord-474750bc30d648c98305972ca5a19be6
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07705042B2

Reaction notes

Loading…