4-(4-Methylpiperazine-1-carbonyl)phenylboronic acid pinacol ester → 1-(2,5-Difluorobenzyl)-3,3-dimethyl-7-[4-(4-methylpiperazine-1-carbonyl)phenyl]-3,4-dihydro-1H-pyrido[2,3-b]pyrazin-2-one

HRID 659371Notes

Reaction equation

HRID 659371 reaction equation
[F:1][C:2]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:3]=1[CH2:4][N:5]1[C:10](=[O:11])[C:9]([CH3:13])([CH3:12])[NH:8][C:7]2[N:14]=[CH:15][C:16](I)=[CH:17][C:6]1=2.[CH3:24][N:25]1[CH2:30][CH2:29][N:28]([C:31]([C:33]2[CH:38]=[CH:37][C:36](B3OC(C)(C)C(C)(C)O3)=[CH:35][CH:34]=2)=[O:32])[CH2:27][CH2:26]1>>[F:1][C:2]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:3]=1[CH2:4][N:5]1[C:10](=[O:11])[C:9]([CH3:13])([CH3:12])[NH:8][C:7]2[N:14]=[CH:15][C:16]([C:36]3[CH:35]=[CH:34][C:33]([C:31]([N:28]4[CH2:29][CH2:30][N:25]([CH3:24])[CH2:26][CH2:27]4)=[O:32])=[CH:38][CH:37]=3)=[CH:17][C:6]1=2

Participants

3

Reactant 2

HCID 27600304-(4-Methylpiperazine-1-carbonyl)phenylboronic acid pinacol esterHCID 578858051-(2,5-Difluorobenzyl)-7-iodo-3,3-dimethyl-3,4-dihydro-1H-pyrido[2,3-b]pyrazin-2-one

Product 1

HCID 578858481-(2,5-Difluorobenzyl)-3,3-dimethyl-7-[4-(4-methylpiperazine-1-carbonyl)phenyl]-3,4-dihydro-1H-pyrido[2,3-b]pyrazin-2-oneYield 55%

Procedure

1-(2,5-Difluorobenzyl)-7-iodo-3,3-dimethyl-3,4-dihydro-1H-pyrido[2,3-b]pyrazin-2-one (45 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 a white solid (55% yield). M.p. 204-206° C., LCMS: m/z=506.16 (M+H+), 1H-NMR (CDCl3, 400 MHz) δ 1.56 (s, 6H), 2.33 (s, 3H), 2.36-2.54 (m, 4H), 3.36-3.54 (m, 2H), 3.73-3.83 (m, 2H), 5.14 (s, 1H), 5.21 (s, 2H), 6.84-6.88 (m, 1H), 6.93-6.98 (m, 1H), 7.07-7.13 (m, 1H), 7.19 (d, J=1.5 Hz, 1H), 7.43 (m, 4H), 8.03 (d, J=2.0 Hz, 1H).

Sources & evidence

ORD record
ord-ceb71732043845bf9b807ee251fa6060
Source dataset
uspto-grants-2011_12
Patent number
US08080561B2

Reaction notes

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