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

HRID 16274

反応式

HRID 16274 の反応式
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]

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
110 °C

実験手順

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].

後処理

  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)

出典と根拠

ORDレコード
ord-ea0bc40c44714cc5bd7c3c70baec4e8f
出典データセット
uspto-grants-2010_06
特許番号
US07737152B2

関連ノート

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