3,4,5-Trimethoxyaniline → HCID 24879529, compound

HRID 16301Notes

Reaction equation

HRID 16301 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]=[C:11]([NH:15][C:16](=[O:18])[CH3:17])[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][CH:12]=[C:11]([NH:15][C:16](=[O:18])[CH3:17])[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 115435012-Chloro-6-(3-acetamidophenyl-oxy)-pyrazine

Product 1

HCID 24879529HCID 24879529, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Using Method EE with 2-chloro-6-(3-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 (81 mg). Yield: 35%. 1H NMR (250 MHz, DMSO-d6) δ 2.03 (s, 3H, CH3—NH), 3.44 (s, 6H, [CH3O]3+5), 3.56 (s, 3H, [CH3O]4), 6.80 (s, 2H, Harom2′+6′), 6.82-6.87 (m, 1H, Harom 5), 7.31-7.49 (m, 2H, Harom 4+6), 7.50 (s, 1H, Harom 2), 7.76 (s, 1H, HPz 5), 7.97 (s, 1H, HPz 3), 9.55 (s, 1H, NH), 10.04 (s, 1H, NH). m/z: 411.2 [(M+H)+, calcd for C21H22N4O5 410.2].

Sources & evidence

ORD record
ord-386f3248987e4eedae6284942ad9db09
Source dataset
uspto-grants-2010_06
Patent number
US07737152B2

Reaction notes

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