Dimethylformamide → 1-{[5-(Chloromethyl)pyrazin-2-yl]methyl}-3-bromo-4-[(2,4-difluorobenzyl)oxy]-6-methylpyridin-2(1H)-one

HRID 1832004ノート

反応式

HRID 1832004 の反応式
N1C(Cl)=NC(Cl)=NC=1[Cl:3].CN(C=O)C.[Br:15][C:16]1[C:17](=[O:42])[N:18]([CH2:33][C:34]2[CH:39]=[N:38][C:37]([CH2:40]O)=[CH:36][N:35]=2)[C:19]([CH3:32])=[CH:20][C:21]=1[O:22][CH2:23][C:24]1[CH:29]=[CH:28][C:27]([F:30])=[CH:26][C:25]=1[F:31]>ClCCl>[Br:15][C:16]1[C:17](=[O:42])[N:18]([CH2:33][C:34]2[CH:39]=[N:38][C:37]([CH2:40][Cl:3])=[CH:36][N:35]=2)[C:19]([CH3:32])=[CH:20][C:21]=1[O:22][CH2:23][C:24]1[CH:29]=[CH:28][C:27]([F:30])=[CH:26][C:25]=1[F:31]

参加物

5

反応物 3

HCID 6228Dimethylformamide2 回HCID 7954Cyanuric chlorideHCID 220506073-Bromo-4-[(2,4-difluorobenzyl)oxy]-1-{[5-(hydroxymethyl)pyrazin-2-yl]methyl}-6-methylpyridin-2(1H)-one

生成物 1

HCID 220511691-{[5-(Chloromethyl)pyrazin-2-yl]methyl}-3-bromo-4-[(2,4-difluorobenzyl)oxy]-6-methylpyridin-2(1H)-one収率 77%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

Cyanurylchloride (0.42 g, .0023 mol) was added to DMF (0.52 mL) and stirred at room temperature for 15 min. Then added dichloromethane (15 mL) followed by the addition of 3-Bromo-4-[(2,4-difluorobenzyl)oxy]-1-{[5-(hydroxymethyl)pyrazin-2-yl]methyl}-6-methylpyridin-2(1H)-one 1.0 g, 0.0022 mol) and reaction mixture was stirred at room temperature under argon atmosphere. After 1 h, an additional 1.0 mL of DMF was added and the reaction was allowed to proceed for another hour, when a clear solution was obtained. The solution was diluted with dichloromethane (20 mL) and washed with water, dried (Na2SO4), and concentrated to dryness under reduced pressure. The residue was triturated with EtOAc, filtered, washed with EtOAc and dried to afford 0.79 g (77%) of the title compound as a pale yellow powder: 1H NMR (CD3OD/400 MHz) δ 8.66 (s, 2H), 7.73 (m, 1H), 7.05 (m, 2H), 6.56 (s, 1H), 5.52 (s, 2H), 5.33 (s, 2H), 4.74 (s, 2H), and 2.57 (s, 3H); ES-HRMS m/z 470.0051 (M+H C19H16N3O2BrClF2 requires 470.0077).

後処理

  1. customreaction mixture
  2. stirringwas stirred at room temperature under argon atmosphere
  3. waitAfter 1 h
  4. waitto proceed for another hour
  5. customwhen a clear solution was obtained
  6. washwashed with water
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated to dryness under reduced pressure
  9. customThe residue was triturated with EtOAc
  10. filtrationfiltered
  11. washwashed with EtOAc
  12. customdried

出典と根拠

ORDレコード
ord-04370ab382ad46b6b944af5251cf3507
出典データセット
uspto-grants-2006_06
特許番号
US07067540B2

反応ノート

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