1-Methyl-4-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)piperazine → 2-(2,5-Difluorophenyl)-1-{7-[2-(4-methylpiperazin-1-yl)pyridin-4-yl]-3,4-dihydro-2H-pyrido[2,3-b]pyrazin-1-yl}ethanone

HRID 659385Notes

Reaction equation

HRID 659385 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[CH2:9][C:10]([N:12]1[CH2:17][CH2:16][NH:15][C:14]2[N:18]=[CH:19][C:20](I)=[CH:21][C:13]1=2)=[O:11].[CH3:23][N:24]1[CH2:29][CH2:28][N:27]([C:30]2[CH:35]=[CH:34][C:33](B3OC(C)(C)C(C)(C)O3)=[CH:32][N:31]=2)[CH2:26][CH2:25]1>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[CH2:9][C:10]([N:12]1[CH2:17][CH2:16][NH:15][C:14]2[N:18]=[CH:19][C:20]([C:34]3[CH:33]=[CH:32][N:31]=[C:30]([N:27]4[CH2:26][CH2:25][N:24]([CH3:23])[CH2:29][CH2:28]4)[CH:35]=3)=[CH:21][C:13]1=2)=[O:11]

Participants

3

Reactant 2

HCID 27696181-Methyl-4-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)piperazineHCID 578860692-(2,5-difluorophenyl)-1-(7-iodo-3,4-dihydro-2H-pyrido[2,3-b]pyrazin-1-yl)ethanone

Product 1

HCID 670917182-(2,5-Difluorophenyl)-1-{7-[2-(4-methylpiperazin-1-yl)pyridin-4-yl]-3,4-dihydro-2H-pyrido[2,3-b]pyrazin-1-yl}ethanoneYield 15%

Procedure

2-(2,5-Difluorophenyl)-1-(7-iodo-3,4-dihydro-2H-pyrido[2,3-b]pyrazin-1-yl)-ethanone (30 mg) was reacted with 1-methyl-4-[5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)pyridin-2-yl]piperazine as in General Procedure 4A to give the title compound as a light yellow solid (15% yield). M.p.>300° C., LCMS: m/z=465.02 (M+H+), 1H-NMR (CDCl3, 400 MHz) δ 2.36 (s, 3H), 2.52-2.57 (m, 2H), 3.52-3.62 (m, 6H), 3.90-3.96 (m, 4H), 5.11 (bs, 1H), 6.70 (d, J=8.8 Hz, 1H), 6.90-7.04 (m, 3H), 7.41-7.58 (m, 2H), 8.07 (s, 1H), 8.32 (s, 1H).

Sources & evidence

ORD record
ord-fc8bbbb784ee4f39af77b08bf4e7a171
Source dataset
uspto-grants-2011_12
Patent number
US08080561B2

Reaction notes

Loading…