4-(4-Methylpiperazine-1-carbonyl)phenylboronic acid pinacol ester → HCID 57885795, compound

HRID 659372Notes

Reaction equation

HRID 659372 reaction equation
[F:1][C:2]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][C:3]=1[CH2:4][N:5]1[CH2:10][C:9]([CH3:12])([CH3:11])[NH:8][C:7]2[N:13]=[CH:14][C:15](I)=[CH:16][C:6]1=2.[CH3:23][N:24]1[CH2:29][CH2:28][N:27]([C:30]([C:32]2[CH:37]=[CH:36][C:35](B3OC(C)(C)C(C)(C)O3)=[CH:34][CH:33]=2)=[O:31])[CH2:26][CH2:25]1>>[F:1][C:2]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][C:3]=1[CH2:4][N:5]1[CH2:10][C:9]([CH3:12])([CH3:11])[NH:8][C:7]2[N:13]=[CH:14][C:15]([C:35]3[CH:34]=[CH:33][C:32]([C:30]([N:27]4[CH2:28][CH2:29][N:24]([CH3:23])[CH2:25][CH2:26]4)=[O:31])=[CH:37][CH:36]=3)=[CH:16][C:6]1=2

Participants

3

Reactant 2

HCID 27600304-(4-Methylpiperazine-1-carbonyl)phenylboronic acid pinacol esterHCID 57885824HCID 57885824, compound

Product 1

HCID 57885795HCID 57885795, compoundYield 55%

Procedure

1-(2,5-Difluorobenzyl)-7-iodo-3,3-dimethyl-1,2,3,4-tetrahydropyrido[2,3-b]pyrazine (44 mg) was reacted with (4-methylpiperazin-1-yl)-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenyl]methanone as in General Procedure 4A to give the title compound as an off-white solid (55% yield). M.p. 191-192° C., LCMS: m/z=492.10 (M+H+), 1H-NMR (CDCl3, 400 MHz) δ 1.34 (s, 6H), 2.32 (s, 3H), 2.38-2.50 (m, 4H), 3.13 (s, 2H), 3.45-3.58 (m, 2H), 3.65-3.85 (m, 2H), 4.52 (s, 2H), 4.90 (bs, 1H), 6.79 (d, J=1.3 Hz, 1H), 6.90-6.97 (m, 1H), 6.99-7.08 (m, 2H), 7.42 (dd, J=8.6 Hz, 4H), 7.74 (d, J=1.5 Hz, 1H).

Sources & evidence

ORD record
ord-c9c83df6f05748b5b4fd454c74b44d54
Source dataset
uspto-grants-2011_12
Patent number
US08080561B2

Reaction notes

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