Triethylamine → 6-Chloro-3-nitro-N2-(quinolin-6-ylmethyl)pyridine-2,4-diamine

HRID 876851Notes

Reaction equation

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

Participants

Conditions

Temperature: 80 °C

Procedure

To a mixture of 2,6-dichloro-3-nitropyridin-4-amine (624 mg, 3 mmol) and quinolin-6-ylmethanamine (316 mg, 2 mmol) in CH3CN (10 mL) was added Et3N (0.5 mL). The reaction mixture was stirred at 80° C. for 1 h. After cooled to room temperature, the mixture was concentrated to afford the title compound (658 mg). MS (m/z): 330 (M+1)+.

Workup

temperatureAfter cooled to room temperature
concentrationthe mixture was concentrated

Sources & evidence

ORD record: ord-2c0f060b34264f2f8064e00cf8393cfa
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08987269B2

Reaction notes

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