2-(4-Methylpiperazin-1-yl)pyridine-4-boronic acid, pinacol ester → 1-(2-Chloro-3,6-difluorobenzyl)-7-[2-(4-methylpiperazin-1-yl)pyridin-4-yl]-1,2,3,4-tetrahydropyrido[2,3-b]pyrazine

HRID 659437Notes

Reaction equation

HRID 659437 reaction equation
[Cl:1][C:2]1[C:25]([F:26])=[CH:24][CH:23]=[C:22]([F:27])[C:3]=1[CH2:4][N:5]1[CH2:10][CH2:9][NH:8][C:7]2[N:11]=[CH:12][C:13]([C:15]3[CH:20]=[CH:19][N:18]=[C:17](Cl)[CH:16]=3)=[CH:14][C:6]1=2.[CH3:28][N:29]1[CH2:34][CH2:33][N:32](C2C=C(B3OC(C)(C)C(C)(C)O3)C=CN=2)[CH2:31][CH2:30]1>>[Cl:1][C:2]1[C:25]([F:26])=[CH:24][CH:23]=[C:22]([F:27])[C:3]=1[CH2:4][N:5]1[CH2:10][CH2:9][NH:8][C:7]2[N:11]=[CH:12][C:13]([C:15]3[CH:20]=[CH:19][N:18]=[C:17]([N:32]4[CH2:33][CH2:34][N:29]([CH3:28])[CH2:30][CH2:31]4)[CH:16]=3)=[CH:14][C:6]1=2

Participants

3

Reactant 2

HCID 27695372-(4-Methylpiperazin-1-yl)pyridine-4-boronic acid, pinacol esterHCID 578858211-(2-Chloro-3,6-difluorobenzyl)-7-(2-chloropyridin-4-yl)-1,2,3,4-tetrahydropyrido[2,3-b]pyrazine

Product 1

HCID 578858911-(2-Chloro-3,6-difluorobenzyl)-7-[2-(4-methylpiperazin-1-yl)pyridin-4-yl]-1,2,3,4-tetrahydropyrido[2,3-b]pyrazineYield 15%

Procedure

1-(2-Chloro-3,6-difluorobenzyl)-7-(2-chloropyridin-4-yl)-1,2,3,4-tetrahydropyrido[2,3-b]pyrazine (88 mg) was coupled to 1-methyl-4-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)pyridin-2-yl]piperazine as in General Procedure 4B to give the title compound as a light yellow solid (15% yield). LCMS: m/z=471.07 (M+H+), 1H-NMR (CDCl3, 400 MHz) δ 2.36 (3H, s), 2.56 (4H, t, J=4.9 Hz), 3.33 (2H, t, J=4.7 Hz), 3.55 (2H, m), 3.62 (4H, t, J=4.9 Hz), 4.53 (2H, s), 5.23 (1H, bs), 6.72 (1H, s), 6.78 (1H, dd, J=5.3, 1.3 Hz), 7.03 (2H, m), 7.12 (1H, m), 7.77 (1H, d, J=1.8 Hz), 8.18 (1H, d, J=5.1 Hz).

Sources & evidence

ORD record
ord-b7480d9103fb4379b3bbd503be9f3244
Source dataset
uspto-grants-2011_12
Patent number
US08080561B2

Reaction notes

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