4-(4-Methylpiperazine-1-carbonyl)phenylboronic acid pinacol ester → (4-Methylpiperazin-1-yl)-(4-{1-[1-(2,4,5-trifluorophenyl)ethyl]-1,2,3,4-tetrahydropyrido[2,3-b]pyrazin-7-yl}phenyl)methanone

HRID 2074630Notes

Reaction equation

HRID 2074630 reaction equation
I[C:2]1[CH:22]=[N:21][C:5]2[NH:6][CH2:7][CH2:8][N:9]([CH:10]([C:12]3[CH:17]=[C:16]([F:18])[C:15]([F:19])=[CH:14][C:13]=3[F:20])[CH3:11])[C:4]=2[CH:3]=1.[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>>[CH3:23][N:24]1[CH2:29][CH2:28][N:27]([C:30]([C:32]2[CH:37]=[CH:36][C:35]([C:2]3[CH:22]=[N:21][C:5]4[NH:6][CH2:7][CH2:8][N:9]([CH:10]([C:12]5[CH:17]=[C:16]([F:18])[C:15]([F:19])=[CH:14][C:13]=5[F:20])[CH3:11])[C:4]=4[CH:3]=3)=[CH:34][CH:33]=2)=[O:31])[CH2:26][CH2:25]1

Participants

3

Reactant 2

HCID 27600304-(4-Methylpiperazine-1-carbonyl)phenylboronic acid pinacol esterHCID 578859497-Iodo-1-[1-(2,4,5-trifluorophenyl)ethyl]-1,2,3,4-tetrahydropyrido[2,3-b]pyrazine

Product 1

HCID 57885810(4-Methylpiperazin-1-yl)-(4-{1-[1-(2,4,5-trifluorophenyl)ethyl]-1,2,3,4-tetrahydropyrido[2,3-b]pyrazin-7-yl}phenyl)methanoneYield 2%

Procedure

7-Iodo-1-[1-(2,4,5-trifluorophenyl)ethyl]-1,2,3,4-tetrahydropyrido[2,3-b]pyrazine (30 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 4B to give the title compound as a yellow solid (2% yield). LCMS: m/z=560.73 (M+H+), 1H-NMR (CDCl3, 400 MHz) δ 1.26 (8H, m), 2.44 (7H, m), 3.64 (4H, m), 7.38 (1H, m), 7.47 (4H, m), 7.61 (4H, m).

Sources & evidence

ORD record
ord-dbe55557f40542bd93728cdb58c704ab
Source dataset
uspto-grants-2011_04
Patent number
US07919502B2

Reaction notes

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