Hydrochloric Acid → 3-{[({6-Fluoro-3'-[(4-methyl-1-piperazinyl)methyl]-3-biphenylyl}methyl)(methyl)amino]carbonyl}benzoic Acid

HRID 564530Notes

Reaction equation

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

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of methyl 3-{[({6-fluoro-3′-[(4-methyl-1-piperazinyl)methyl]-3-biphenylyl}methyl)(methyl)amino]carbonyl}benzoate (0.20 g, 0.409 mmol) in MeOH/H2O (1.2/0.6 mL) was added LiOH.H2O (0.086 g, 2.05 mmol). The mixture was heated in a microwave at 80° C. for 30 min following which it was acidified with HCl, concentrated and the concentrate purified using a Gilson HPLC to afford the title compound 0.221 g (quantitative). LC-MS m/z 476 (M+H)+.

Workup

concentrationconcentrated
customthe concentrate purified

Sources & evidence

ORD record: ord-3cf6cb01a7d046bda305a34ec4ed2e9b
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08067408B2

Reaction notes

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