Hydrochloric Acid → N-isopropyl-2,8-dimethylquinoline-7-carboxamide

HRID 339023Notes

Reaction equation

[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([CH3:15])[C:6]([C:12]([OH:14])=O)=[CH:7][CH:8]=2)[N:3]=1.[CH:16]([NH2:19])([CH3:18])[CH3:17].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.Cl>CC#N.O>[CH:16]([NH:19][C:12]([C:6]1[C:5]([CH3:15])=[C:4]2[C:9]([CH:10]=[CH:11][C:2]([CH3:1])=[N:3]2)=[CH:8][CH:7]=1)=[O:14])([CH3:18])[CH3:17]

Participants

Conditions

Temperature: 0 °C

Procedure

A mixture of 2,8-dimethylquinoline-7-carboxylic acid (0.20 g, 0.994 mmol), isopropylamine (0.102 mL, 1.19 mmol) and HATU (0.491 g, 1.29 mmol) in anhydrous MeCN (5 mL) under a nitrogen atmosphere was cooled to 0° C. in an ice bath. To the cooled mixture was added dropwise DIEA (0.69 mL, 3.98 mmol) and the resulting mixture stirred at ambient temperature for 18 hours. The mixture was diluted with water, neutralized with aqueous 1N HCl and extracted with ethyl acetate. The combined organic extracts were washed with water and brine, dried (MgSO4), filtered and concentrated under reduced pressure. The residue was purified by reverse phase chromatography (Biotage SP4, 25M C-18, 5-60% MeCN—H2O) to afford N-isopropyl-2,8-dimethylquinoline-7-carboxamide (0.223 g, 93%).

Workup

extractionextracted with ethyl acetate
washThe combined organic extracts were washed with water and brine
dry with materialdried (MgSO4)
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe residue was purified by reverse phase chromatography (Biotage SP4, 25M C-18, 5-60% MeCN—H2O)

Sources & evidence

ORD record: ord-b518f8e5a55c45519ab8cf368d964e54
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08889704B2

Reaction notes

Loading…