3,4,5-Trimethoxyaniline → 2-(3,4,5-Trimethoxyphenylamino)-6-(4-acetamidophenyl-oxy)-pyrazine

HRID 16302Notes

Reaction equation

HRID 16302 reaction equation
Cl[C:2]1[CH:7]=[N:6][CH:5]=[C:4]([O:8][C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16](=[O:18])[CH3:17])=[CH:11][CH:10]=2)[N:3]=1.[CH3:19][O:20][C:21]1[CH:22]=[C:23]([CH:25]=[C:26]([O:30][CH3:31])[C:27]=1[O:28][CH3:29])[NH2:24]>CCOC(C)=O>[CH3:31][O:30][C:26]1[CH:25]=[C:23]([NH:24][C:2]2[CH:7]=[N:6][CH:5]=[C:4]([O:8][C:9]3[CH:14]=[CH:13][C:12]([NH:15][C:16](=[O:18])[CH3:17])=[CH:11][CH:10]=3)[N:3]=2)[CH:22]=[C:21]([O:20][CH3:19])[C:27]=1[O:28][CH3:29]

Participants

4

Reactant 2

HCID 322853,4,5-TrimethoxyanilineHCID 593434822-Chloro-6-(4-acetamidophenyl-oxy)-pyrazine

Product 1

HCID 248792642-(3,4,5-Trimethoxyphenylamino)-6-(4-acetamidophenyl-oxy)-pyrazineYield 37%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Using Method EE with 2-chloro-6-(4-acetamidophenyl-oxy)-pyrazine (150 mg, 0.57 mmol) and 3,4,5-trimethoxyaniline (125 mg, 0.68 mmol), and crystallisation (AcOEt), the title compound was obtained (87 mg). Yield: 37%. 1H NMR (250 MHz, DMSO-d6) δ 2.07 (s, 3H, CH3—NH), 3.43 (s, 6H, [CH3O]3+5), 3.55 (s, 3H, [CH3O]4), 6.77 (s, 2H, Harom2′+6′), 7.13 (d, 2H, Harom 3+5, J=8.9 Hz), 7.60 (d, 2H, Harom 2+6, J=8.9 Hz), 7.73 (s, 1H, HPz 5), 7.93 (s, 1H, HPz 3), 9.51 (s, 1H, NH), 9.98 (s, 1H, NH). m/z: 411.2 [(M+H)+, calcd for C21H22N4O5 410.2].

Sources & evidence

ORD record
ord-0727ca19a2fb40459eb703803e7ca0d4
Source dataset
uspto-grants-2010_06
Patent number
US07737152B2

Reaction notes

Loading…