4-(4-Methylpiperazine-1-carbonyl)phenylboronic acid pinacol ester → HCID 57886120, compound

HRID 659364Notes

Reaction equation

I[C:2]1[CH:22]=[N:21][C:5]2[NH:6][CH2:7][C:8](=[O:20])[N:9]([CH2:10][C:11]3[CH:16]=[C:15]([F:17])[C:14]([F:18])=[CH:13][C:12]=3[F:19])[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][C:8](=[O:20])[N:9]([CH2:10][C:11]5[CH:16]=[C:15]([F:17])[C:14]([F:18])=[CH:13][C:12]=5[F:19])[C:4]=4[CH:3]=3)=[CH:34][CH:33]=2)=[O:31])[CH2:26][CH2:25]1

Participants

Reactant 2

HCID 27600304-(4-Methylpiperazine-1-carbonyl)phenylboronic acid pinacol ester

HCID 57885938HCID 57885938, compound

Product 1

HCID 57886120HCID 57886120, compoundYield 32%

Procedure

7-Iodo-1-(2,4,5-trifluorobenzyl)-3,4-dihydro-1H-pyrido[2,3-b]pyrazin-2-one (42 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 (32% yield). M.p. 238° C., LCMS: m/z=496.00 (M+H+), 1H-NMR (CDCl3, 400 MHz) δ 2.33 (s, 3H), 2.35-2.53 (m, 4H), 3.43-3.58 (m, 2H), 3.72-3.84 (m, 2H), 4.33 (s, 2H), 5.11 (s, 1H), 5.30 (s, 2H), 6.97-7.03 (m, 1H), 7.05-7.14 (m, 1H), 7.21 (s, 1H), 7.45 (dd, J=8.1 Hz, 4H), 8.02 (s, 1H).

Sources & evidence

ORD record: ord-869abab68b2449c5a8d628eb539a9bf4
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08080561B2

Reaction notes

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