3,4,5-Trimethoxyaniline → HCID 24879527, compound

HRID 16298Notes

Reaction equation

HRID 16298 reaction equation
Cl[C:2]1[CH:7]=[N:6][CH:5]=[C:4]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:3]=1.[CH3:21][O:22][C:23]1[CH:24]=[C:25]([CH:27]=[C:28]([O:32][CH3:33])[C:29]=1[O:30][CH3:31])[NH2:26]>CCOC(C)=O>[CH3:33][O:32][C:28]1[CH:27]=[C:25]([NH:26][C:2]2[CH:7]=[N:6][CH:5]=[C:4]([O:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[N:3]=2)[CH:24]=[C:23]([O:22][CH3:21])[C:29]=1[O:30][CH3:31]

Participants

4

Reactant 2

HCID 322853,4,5-TrimethoxyanilineHCID 593434912-Chloro-6-(2-phenyl-phenyl-oxy)-pyrazine

Product 1

HCID 24879527HCID 24879527, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Using Method EE with 2-chloro-6-[(2-phenyl)-phenyl-oxy]-pyrazine (110 mg, 0.39 mmol) and 3,4,5-trimethoxyaniline (84 mg, 0.46 mmol), and purification by column chromatography (AcOEt), the title compound was obtained (101 mg). Yield: 60%. 1H NMR (250 MHz, DMSO-d6) δ 3.41 (s, 6H, [CH3O]3+5), 3.55 (s, 3H, [CH3O]4), 6.79 (s, 2H, Harom2′+6′), 7.22-7.49 (m, 9H, Harom), 7.66 (s, 1H, HPz 5) 7.88 (s, 1H, HPz 3), 9.51 (s, 1H, NH).

Sources & evidence

ORD record
ord-b68d5eaacba741c5a12408d158f3219b
Source dataset
uspto-grants-2010_06
Patent number
US07737152B2

Reaction notes

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