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

HRID 1832004노트

반응식

HRID 1832004 반응식
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]

참가 물질

5

반응물 3

HCID 6228Dimethylformamide2회HCID 7954Cyanuric chlorideHCID 220506073-Bromo-4-[(2,4-difluorobenzyl)oxy]-1-{[5-(hydroxymethyl)pyrazin-2-yl]methyl}-6-methylpyridin-2(1H)-one

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-04370ab382ad46b6b944af5251cf3507
출처 데이터셋
uspto-grants-2006_06
특허 번호
US07067540B2

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