Lithium Hydroxide → HCID 70976470, compound

HRID 882223Notes

Reaction equation

[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]3[CH:19]=[CH:18][C:17]([CH2:20][C:21]([O:23]CC)=[O:22])=[CH:16][CH:15]=3)=[CH:11][CH:12]=2)[C@H:7]([NH:26][C:27]2[CH:32]=[CH:31][C:30]([C:33]#[N:34])=[CH:29][N:28]=2)[CH2:6][C@@H:5]1[CH3:35])(=[O:3])[CH3:2].[OH-].[Li+]>CO>[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]3[CH:15]=[CH:16][C:17]([CH2:20][C:21]([OH:23])=[O:22])=[CH:18][CH:19]=3)=[CH:11][CH:12]=2)[C@H:7]([NH:26][C:27]2[CH:32]=[CH:31][C:30]([C:33]#[N:34])=[CH:29][N:28]=2)[CH2:6][C@@H:5]1[CH3:35])(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 40 °C

Procedure

To a solution of ethyl 2-(4-((2S,4R)-1-acetyl-4-((5-cyanopyridin-2-yl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)phenyl)acetate (for a preparation see Intermediate 8) (300 mg, 0.640 mmol) in MeOH (5 mL) was added lithium hydroxide solution (0.768 mL, 0.768 mmol). The resulting mixture was stirred at 40° C. for 2 h, whereupon it was concentrated under vacuum to give the crude lithium carboxylate of 2-(4-((2S,4R)-1-acetyl-4-((5-cyanopyridin-2-yl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)phenyl)acetic acid (286 mg, 100%) as a white solid which was used in the next step without further purification. LCMS (Formate, 2 min), Rt=1.10 min, MH+=433.

Workup

concentrationwas concentrated under vacuum

Sources & evidence

ORD record: ord-2e2b0d45b69d41a4a648e6db84f48ca6
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08993554B2

Reaction notes

Loading…