Lithium Hydroxide → HCID 66762476, compound

HRID 578639Notes

Reaction equation

HRID 578639 reaction equation
[F:1][C:2]([F:24])([F:23])[C:3]1[CH:4]=[C:5]([CH:20]=[CH:21][CH:22]=1)[CH2:6][NH:7][C:8]1[C:17]2[C:12](=[C:13]([C:18]#[N:19])[CH:14]=[CH:15][CH:16]=2)[N:11]=[CH:10][CH:9]=1.[Li+].[OH-:26]>O1CCOCC1>[F:24][C:2]([F:23])([F:1])[C:3]1[CH:4]=[C:5]([CH:20]=[CH:21][CH:22]=1)[CH2:6][NH:7][C:8]1[C:17]2[C:12](=[C:13]([C:18]([NH2:19])=[O:26])[CH:14]=[CH:15][CH:16]=2)[N:11]=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 66763182HCID 66763182, compound

Product 1

HCID 66762476HCID 66762476, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 4-{[3-(trifluoromethyl)benzyl]amino}quinoline-8-carbonitrile (20 mg, 0.05 mmol) in 2 mL of dioxane, 2N LiOH solution (250 μL, 0.5 mmol, 10 equiv.) was added. The resulting mixture was heated at 90° C. by microwave for 20 min. After work-up, the crude was purified by preparative HPLC to yield the title compound as a white solid in 34% yield. 1HNMR (in DMSO): 4.92 (d, J=5.8 Hz, 2H), 6.93 (d, J=7.4 Hz, 1H), 7.62 (t, J=7.7 Hz, 1H), 7.69 (d, J=8.1 Hz, 1H), 7.74 (d, J=7.3 Hz, 1H), 7.85 9s, 1H), 7.87 (d, J=8.1 Hz, 1H), 8.22 (s, 1H), 8.48-8.54 (m, 2H), 8.75 (s, 1H), 8.80 (d, J=8.4 Hz, 1H), 10.06 (s, 1H). Mass: M+H+: 346.

Workup

  1. customAfter work-up, the crude was purified by preparative HPLC

Sources & evidence

ORD record
ord-a4227a2151974eebac5c828ee096043f
Source dataset
uspto-grants-2015_05
Patent number
US09040560B2

Reaction notes

Loading…