N-(2-aminoethyl)acetamide → HCID 86669822, compound

HRID 1620266Notes

Reaction equation

Cl[C:2]1[C:11]([CH:12]=[O:13])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:14][CH3:15])[CH:8]=2)[N:3]=1.[NH2:16][CH2:17][CH2:18][NH:19][C:20](=[O:22])[CH3:21]>C1COCC1>[CH:12]([C:11]1[C:2]([NH:16][CH2:17][CH2:18][NH:19][C:20](=[O:22])[CH3:21])=[N:3][C:4]2[C:9]([CH:10]=1)=[CH:8][C:7]([O:14][CH3:15])=[CH:6][CH:5]=2)=[O:13]

Participants

Conditions

Temperature: 160 °C

Procedure

To a stirred solution of 2-chloro-6-methoxyquinoline-3-carbaldehyde (2.00 g, 9.0 mmol) in THF (10 mL) in a 20 mL microwave vial equipped with a magnetic stirrer was added N-(2-aminoethyl)acetamide (2.76 g, 27.1 mmol) and the reaction mixture was stirred for 1 h at 160° C. under microwave irradiation. After cooling to RT, the volatiles were removed at 40° C. under vacuum and the resulting yellow oil was taken up with CH2Cl2 (100 mL). This organic solution was washed with brine (2×10 mL), dried over MgSO4, filtered, and concentrated under vacuum. The residue was finally purified by column chromatography (SiO2, eluent cyclohexane:EtOAc=100:0 to 0:100) to give N-(2-(3-formyl-6-methoxyquinolin-2-ylamino)ethyl)acetamide SLA 41168 as an orange solid (601 mg, 23% yield).

Workup

temperatureAfter cooling to RT
customthe volatiles were removed at 40° C. under vacuum
washThis organic solution was washed with brine (2×10 mL)
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated under vacuum
customThe residue was finally purified by column chromatography (SiO2, eluent cyclohexane:EtOAc=100:0 to 0:100)

Sources & evidence

ORD record: ord-1a620c36cc84491e80f41b0070fd5b9c
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08772316B2

Reaction notes

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