Triethylamine → 6-Chloro-2-[1-(naphthalen-2-ylcarbamoyl)-ethylamino]-quinoline-3-carboxylic acid

HRID 2065627

Reaction equation

Cl[C:2]1[C:11]([C:12]([OH:14])=[O:13])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([Cl:15])[CH:8]=2)[N:3]=1.[CH:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=[CH:18][C:17]=1[NH:26][C:27](=[O:31])[CH:28]([CH3:30])[NH2:29].C(N(CC)CC)C>O1CCOCC1>[Cl:15][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[N:3]=[C:2]([NH:29][CH:28]([C:27](=[O:31])[NH:26][C:17]1[CH:18]=[CH:19][C:20]3[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:16]=1)[CH3:30])[C:11]([C:12]([OH:14])=[O:13])=[CH:10]2

Participants

Conditions

Temperature: 135 °C

Procedure

A mixture of 2,6-dichloroquinoline-3-carboxylic acid (194 mg, 0.8 mmol), DL-alanine-β-naphthylamide (251 mg, 1 mmol) and triethylamine (900 mg, 8.9 mmol) in dioxane (1 mL) is stirred for 24 h at 135° C. in closed reaction vial. After evaporation of solvents in vacuo, the residue is acidified by addition of 2N HCl, and the precipitated solid is collected on filter, washed with water and recrystallized from MeOH-water to give the title compound (200 mg, 60%) as yellow needles.

Workup

customAfter evaporation of solvents in vacuo
additionthe residue is acidified by addition of 2N HCl
customthe precipitated solid is collected
filtrationon filter
washwashed with water
customrecrystallized from MeOH-water

Sources & evidence

ORD record: ord-b9f374a02f3847068c962de208210b48
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08288549B2

Linked notes

Loading…