Diisopropylethylamine → HCID 68194165, compound

HRID 1520164Notes

Reaction equation

Cl[C:2]1[C:3](=[O:16])[NH:4][C:5]2[C:10]([N:11]=1)=[CH:9][C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:7][CH:6]=2.CCN(C(C)C)C(C)C.Cl.[CH3:27][N:28]([CH3:39])[C:29]1[CH:30]=[C:31]2[C:36](=[CH:37][CH:38]=1)[NH:35][CH2:34][CH2:33][CH2:32]2>CN1C(=O)CCC1.O>[CH3:27][N:28]([CH3:39])[C:29]1[CH:30]=[C:31]2[C:36](=[CH:37][CH:38]=1)[N:35]([C:2]1[C:3](=[O:16])[NH:4][C:5]3[C:10]([N:11]=1)=[CH:9][C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:7][CH:6]=3)[CH2:34][CH2:33][CH2:32]2

Participants

Conditions

Temperature: 130 °C

Procedure

To a solution of methyl 3-chloro-2-oxo-1,2-dihydroquinoxaline-6-carboxylate (420 mg, 1.76 mmol,) in NMP (3 mL) was added DIEA (343 mg, 2.65 mmol), N,N-dimethyl-1,2,3,4-tetrahydroquinolin-6-amine hydrochloride (400 mg, crude) and the reaction was stirred for 2 h at 130° C. in an oil bath. The resulting solution was diluted with water (100 mL), and the solids were collected by filtration to give methyl 3-[6-(dimethylamino)-1,2,3,4-tetrahydroquinolin-1-yl]-2-oxo-1,2-dihydroquinoxaline-6-carboxylate as a red solid (260 mg, 39%).

Workup

filtrationthe solids were collected by filtration

Sources & evidence

ORD record: ord-fcfab27a993445c3a9b21f8e6628018b
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09073902B2

Reaction notes

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