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

HRID 16274

Reaktionsgleichung

Reaktionsgleichung von HRID 16274
Br[C:2]1[C:7]([NH:8][C:9](=[O:11])[CH3:10])=[N:6][CH:5]=[C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([NH:18][C:19](=[O:21])[CH3:20])[CH:13]=2)[N:3]=1.[CH3:22][O:23][C:24]1[CH:25]=[C:26]([CH:28]=[C:29]([O:33][CH3:34])[C:30]=1[O:31][CH3:32])[NH2:27].CC(C)([O-])C.[Na+].C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1>C1(C)C=CC=CC=1>[CH3:34][O:33][C:29]1[CH:28]=[C:26]([NH:27][C:2]2[C:7]([NH:8][C:9](=[O:11])[CH3:10])=[N:6][CH:5]=[C:4]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([NH:18][C:19](=[O:21])[CH3:20])[CH:13]=3)[N:3]=2)[CH:25]=[C:24]([O:23][CH3:22])[C:30]=1[O:31][CH3:32]

Komponenten

6

Edukt 4

HCID 322853,4,5-TrimethoxyanilineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 23676156Sodium t-butoxideHCID 593434502-Bromo-3-acetamido-6-(3-acetamidophenyl)pyrazine

Produkt 1

HCID 115832652-(3,4,5-Trimethoxyphenylamino)-3-acetamido-6-(3-acetamidophenyl)pyrazineAusbeute 17 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

Method AA. In a tube suitable for microwave irradiation provided with stirring and an argon atmosphere were placed 2-bromo-3-acetamido-6-(3-acetamidophenyl)pyrazine (32 mg, 0.09164 mmol), 3,4,5-trimethoxyaniline (33.6 mg, 0.1833 mmol), sodium tert-butoxide (18 mg, 0.1833 mmol), Pd(0)2 dba3 (8.4 mg, 9.164 μmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (Xant phos) (5.3 mg, 9.164 μmol) and dry toluene 1.5 mL). The tube was heated by microwave irradiation at 110° C. for 30 minutes. The reaction crude was filtered and the precipitate washed with boiling ethyl acetate (30 mL). The organic layers were evaporated under vacuum and the resulting crude was chromatographed (eluent: mixture of ethyl acetate and methanol; 9:1) to produce 7 mg of title compound. Yield: 17%. 1H NMR (250 MHz, DMSO-d6) δ 2.06 (s, 3H), 2.17 (s, 3H), 3.64 (s, 3H), 3.77 (s, 9H), 7.24 (s, 2H), 7.42 (t, 1H, J=8.0 Hz), 7.64 (d, 1H, J=7.7 Hz), 7.73 (d, 1H, J=7.9 Hz), 8.22 (bs, 1H), 8.28 (s, 1H), 8.52 (s, 1H), 10.07 (s, 1H), 10.21 (s, 1H). m/z 452.2 [(M+H)+ calcd for C23H25N5O5 451.2].

Aufarbeitung

  1. customIn a tube suitable for microwave irradiation
  2. customprovided
  3. customThe reaction crude
  4. filtrationwas filtered
  5. washthe precipitate washed with boiling ethyl acetate (30 mL)
  6. customThe organic layers were evaporated under vacuum
  7. customthe resulting crude was chromatographed
  8. addition(eluent: mixture of ethyl acetate and methanol; 9:1)

Quellen und Nachweise

ORD-Eintrag
ord-ea0bc40c44714cc5bd7c3c70baec4e8f
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07737152B2

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