B-[2-(1-Piperazinyl)-4-pyridinyl]boronic acid → HCID 46871653, compound

HRID 659442Notes

Reaction equation

HRID 659442 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:20]([F:23])([F:22])[F:21])=[C:6]([CH:19]=1)[CH2:7][N:8]1[CH2:13][CH2:12][NH:11][C:10]2[N:14]=[CH:15][C:16](I)=[CH:17][C:9]1=2.[N:24]1([C:30]2[CH:35]=[C:34](B(O)O)[CH:33]=[CH:32][N:31]=2)[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:20]([F:23])([F:22])[F:21])=[C:6]([CH:19]=1)[CH2:7][N:8]1[CH2:13][CH2:12][NH:11][C:10]2[N:14]=[CH:15][C:16]([C:34]3[CH:33]=[CH:32][N:31]=[C:30]([N:24]4[CH2:25][CH2:26][NH:27][CH2:28][CH2:29]4)[CH:35]=3)=[CH:17][C:9]1=2

Participants

3

Reactant 2

HCID 53443448B-[2-(1-Piperazinyl)-4-pyridinyl]boronic acidHCID 578860851-(5-Chloro-2-trifluoromethylbenzyl)-7-iodo-1,2,3,4-tetrahydropyrido[2,3-b]pyrazine

Product 1

HCID 46871653HCID 46871653, compound

Procedure

1-[5-Chloro-2-(trifluoromethyl)benzyl]-7-iodo-1,2,3,4-tetrahydro-pyrido[2,3-b]pyrazine (293 mg) was reacted with 2-(piperazin-1-yl)pyridine-4-boronic acid, pinacol ester as in General Procedure 4B to give the title compound as an off-white solid. m.p.=189° C., LCMS: m/z=489.08 (M+H+), 1H-NMR (CDCl3, 400 MHz) δ 2.98 (4H, m), 3.49 (6H, m), 3.71 (2H, m), 4.61 (2H, s), 5.29 (1H, s), 5.34 (1H, bs), 6.55 (2H, m), 6.64 (1H, dd, J=5.2, 1.4 Hz), 7.36 (1H, d, J=8.1 Hz), 7.52 (1H, s), 7.64 (1H, d, J=8.3 Hz), 7.77 (1H, d, J=2.0 Hz), 8.12 (1H, d, J=5.3 Hz).

Sources & evidence

ORD record
ord-2fbced28a8ad4db4ac95060195198b7e
Source dataset
uspto-grants-2011_12
Patent number
US08080561B2

Reaction notes

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