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

HRID 15827Notes

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-02a042b990bc49c2b4d409c69276c541
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07732600B2

Reaction notes

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