3,4,5-Trimethoxyaniline → 4-({6-[(3,4,5-trimethoxyphenyl)amino]pyrazin-2-yl}oxy)-2,3-dihydro-1H-inden-1-one

HRID 16303Notes

Reaction equation

HRID 16303 reaction equation
Cl[C:2]1[CH:7]=[N:6][CH:5]=[C:4]([O:8][C:9]2[C:10]3[CH2:11][CH2:12][C:13](=[O:18])[C:14]=3[CH:15]=[CH:16][CH:17]=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[C:10]4[CH2:11][CH2:12][C:13](=[O:18])[C:14]=4[CH:15]=[CH:16][CH:17]=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 593434162-Chloro-6-(indanone-4-oxy)-pyrazine

Product 1

HCID 248794664-({6-[(3,4,5-trimethoxyphenyl)amino]pyrazin-2-yl}oxy)-2,3-dihydro-1H-inden-1-oneYield 23%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Using Method EE with 2-chloro-6-(indanone-4-oxy)-pyrazine (200 mg, 0.77 mmol) and 3,4,5-trimethoxyaniline (169 mg, 0.92 mmol), and purification by column chromatography (AcOEt), the title compound was obtained (71 mg). Yield: 23%. 1H NMR (250 MHz, DMSO-d6) δ 2.69 (t, 2H, H3, J=3.7 Hz), 2.98 (t, 2H, H2, J=5.2 Hz), 3.43 (s, 6H, [CH3O]3+5), 3.59 (s, 3H, [CH3O]4), 6.75 (s, 2H, Harom2′+6′), 7.56-7.62 (m, 3H, Harom), 7.90 (s, 1H, HPz 5), 8.04 (s, 1H, HPz 3), 9.62 (s, 1H, NH). m/z: 408.1 [(M+H)+, calcd for C22H21N3O5 407.1].

Sources & evidence

ORD record
ord-2ef800a275094fa0bf200ff020a4f072
Source dataset
uspto-grants-2010_06
Patent number
US07737152B2

Reaction notes

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