4-Fluoroaniline → HCID 24879392, compound

HRID 16270Notes

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:28]=[CH:27][C:25]([NH2:26])=[CH:24][CH:23]=1>>[F:21][C:22]1[CH:28]=[CH:27][C:25]([NH:26][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:24][CH:23]=1

Participants

Reactant 2

HCID 97314-Fluoroaniline

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

Product 1

HCID 24879392HCID 24879392, compoundYield 28%

Procedure

Using Method R, with 200 mg of 2-(3,4,5-trimethoxyphenylamino)-6-chloropyrazine (all amounts scaled accordingly) and 4-fluoroaniline, 72 mg of title compound were obtained. Yield: 28%. 1H NMR (250 MHz, DMSO-d6) δ 3.62 (s, 9H), 6.83 (s, 2H), 7.06 (t, 2H, J=9.0 Hz), 7.51 (s, 1H), 7.57 (d, 2H, J=9.1 Hz), 9.05 (s, 1H), 9.14 (s, 1H). 13C NMR (62.5 MHz, DMSO-d6) δ 55.56, 60.12, 97.01, 114.94, 115.29, 120.38, 120.50, 121.62, 121.83, 132.29, 137.19, 137.22, 150.15, 152.84. m/z 371.2 [(M+H)+ calcd for C19H19FN4O3 370.1].

Sources & evidence

ORD record: ord-06e9eefb3dfc466fb08968a16aedb4a0
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07737152B2

Reaction notes

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