3-Fluoroaniline → N2-(3-fluorophenyl)-N6-(3,4,5-trimethoxyphenyl)pyrazine-2,6-diamine

HRID 16269

Reaction equation

HRID 16269 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:13][C:14]2[CH:19]=[N:18][CH:17]=[C:16](Cl)[N:15]=2)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].[F:21][C:22]1[CH:23]=[C:24]([CH:26]=[CH:27][CH:28]=1)[NH2:25]>>[F:21][C:22]1[CH:23]=[C:24]([NH:25][C:16]2[CH:17]=[N:18][CH:19]=[C:14]([NH:13][C:5]3[CH:4]=[C:3]([O:2][CH3:1])[C:8]([O:9][CH3:10])=[C:7]([O:11][CH3:12])[CH:6]=3)[N:15]=2)[CH:26]=[CH:27][CH:28]=1

Participants

3

Reactant 2

HCID 97423-FluoroanilineHCID 116090492-(3,4,5-Trimethoxyphenylamino)-6-chloropyrazine

Product 1

HCID 24879204N2-(3-fluorophenyl)-N6-(3,4,5-trimethoxyphenyl)pyrazine-2,6-diamineYield 23%

Procedure

Using Method R, with 200 mg of 2-(3,4,5-trimethoxyphenylamino)-6-chloropyrazine (all amounts scaled accordingly) and 3-fluoroaniline, 60 mg of title compound were obtained. Yield: 23%. 1H NMR (250 MHz, DMSO-d6) δ 3.62 (s, 3H), 3.65 (s, 6H), 6.65-6.72 (m, 1H), 6.81 (s, 2H), 7.24 (m, 2H), 7.56 (s, 1H), 7.58 (s, 1H), 7.67 (d, 1H, J=13.0 Hz), 9.12 (s, 1H), 9.41 (s, 1H). 13C NMR (62.5 MHz, DMSO-d6) δ 55.45, 60.07, 97.24, 106.71, 107.05, 114.04, 122.16, 122.49, 130.14, 132.43, 136.55, 142.71, 142.89, 149.52, 150.10, 152.89.

Sources & evidence

ORD record
ord-f650a93ca9c844c3988c82bc1e47cea7
Source dataset
uspto-grants-2010_06
Patent number
US07737152B2

Linked notes

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