Hydrochloric Acid → 2-Methyl-5-(4-{2-[3-(1H-pyrazol-1-yl)phenyl]ethyl}-1-piperazinyl)quinoline

HRID 734546Notes

Reaction equation

[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[N:12]2[CH2:17][CH2:16][N:15]([C:18](=O)[CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([N:26]4[CH:30]=[CH:29][CH:28]=[N:27]4)[CH:21]=3)[CH2:14][CH2:13]2)[N:3]=1.Cl>O1CCCC1>[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[N:12]2[CH2:17][CH2:16][N:15]([CH2:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([N:26]4[CH:30]=[CH:29][CH:28]=[N:27]4)[CH:21]=3)[CH2:14][CH2:13]2)[N:3]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A 1M tetrahydrofuran solution of borane-tetrahydrofuran complex (3 eq) was added to a stirred solution of 2-methyl-5-(4-{[3-(1H-pyrazol-1-yl)phenyl]acetyl}-1-piperazinyl)quinoline (E97) (1 eq) in tetrahydrofuran at room temperature under an inert atmosphere. The solution was heated to 60° C. for 3 hrs. An aqueous 3N solution of HCl was added and the solution was stirred at room temperature for 12 hrs. The solvent was removed under reduced pressure. The crude material was purified by SCX cartridge affording the title compound in 52% yield.

Workup

customThe solvent was removed under reduced pressure
customThe crude material was purified by SCX cartridge

Sources & evidence

ORD record: ord-4c06f55dff6144299a40020aec569ebe
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07592346B2

Reaction notes

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