Triethylamine → N-(6-chloro-3-nitro-2-(quinolin-6-ylmethylamino)pyridin-4-yl)acetamide

HRID 1890603Notes

Reaction equation

Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([NH:11][C:12](=[O:14])[CH3:13])[CH:5]=[C:4]([Cl:15])[N:3]=1.[N:16]1[C:25]2[C:20](=[CH:21][C:22]([CH2:26][NH2:27])=[CH:23][CH:24]=2)[CH:19]=[CH:18][CH:17]=1.CCN(CC)CC>CC#N>[Cl:15][C:4]1[N:3]=[C:2]([NH:27][CH2:26][C:22]2[CH:21]=[C:20]3[C:25](=[CH:24][CH:23]=2)[N:16]=[CH:17][CH:18]=[CH:19]3)[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([NH:11][C:12](=[O:14])[CH3:13])[CH:5]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a mixture of N-(2,6-dichloro-3-nitropyridin-4-yl)acetamide (240 mg, 0.96 mmol) and quinolin-6-ylmethanamine (150 mg, 0.96 mmol) in CH3CN (10 mL) was added Et3N (0.5 mL). The reaction mixture was stirred at 80° C. for 1 h. After being cooled to room temperature, the mixture was purified by chromatography on silica gel eluting with DCM/MeOH=50/1 to afford the title compound (220 mg). MS (m/z): 372 (M+1)+.

Workup

temperatureAfter being cooled to room temperature
customthe mixture was purified by chromatography on silica gel eluting with DCM/MeOH=50/1

Sources & evidence

ORD record: ord-a99af18bd84c47f28c8f64140076a0dc
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08507487B2

Reaction notes

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