1-[4-(Benzyloxy)-2-fluorophenyl]-N,5-dimethoxy-N-methyl-4-oxo-1,4-dihydropyridazine-3-carboxamide → 3-Acetyl-1-[4-(benzyloxy)-2-fluorophenyl]-5-methoxypyridazin-4(1H)-one

HRID 1624631노트

반응식

HRID 1624631 반응식
[CH3:1][Mg+].[Br-].[CH2:4]([O:11][C:12]1[CH:17]=[CH:16][C:15]([N:18]2[CH:23]=[C:22]([O:24][CH3:25])[C:21](=[O:26])[C:20]([C:27](N(OC)C)=[O:28])=[N:19]2)=[C:14]([F:33])[CH:13]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>C1COCC1>[C:27]([C:20]1[C:21](=[O:26])[C:22]([O:24][CH3:25])=[CH:23][N:18]([C:15]2[CH:16]=[CH:17][C:12]([O:11][CH2:4][C:5]3[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=3)=[CH:13][C:14]=2[F:33])[N:19]=1)(=[O:28])[CH3:1]

참가 물질

4

반응물 2

HCID 866439351-[4-(Benzyloxy)-2-fluorophenyl]-N,5-dimethoxy-N-methyl-4-oxo-1,4-dihydropyridazine-3-carboxamideHCID 178418689HCID 178418689, 화합물

생성물 1

HCID 594362803-Acetyl-1-[4-(benzyloxy)-2-fluorophenyl]-5-methoxypyridazin-4(1H)-one수율 85%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

MeMgBr (1 M solution in THF, 56.4 mL, 56.4 mmol) was added dropwise at −78° C. to a solution of 1-[4-(benzyloxy)-2-fluorophenyl]-N,5-dimethoxy-N-methyl-4-oxo-1,4-dihydropyridazine-3-carboxamide (7.77 g, 18.8 mmol) in THF (120 mL). After stirring for 1 h, the reaction mixture was quenched with 1 M HCl aqueous solution and extracted with AcOEt. The extract was washed with brine, dried over MgSO4, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography eluting with AcOEt and crystallized from hexane/AcOEt to give the title compound (5.86 g, 85% yield) as a pale yellow solid: mp 101-103° C.; 1H NMR (300 MHz, CDCl3): δ ppm 2.67 (3H, s), 3.89 (3H, s), 5.13 (2H, s), 6.84-6.93 (2H, m), 7.34-7.44 (5H, m), 7.48-7.55 (1H, m), 7.69 (1H, d, J=2.3 Hz). Anal. Calcd for C20H17FN2O4: C, 65.21; H, 4.65; N, 7.60. Found: C, 65.37; H, 4.68; N, 7.47.

후처리

  1. customthe reaction mixture was quenched with 1 M HCl aqueous solution
  2. extractionextracted with AcOEt
  3. washThe extract was washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography
  7. washeluting with AcOEt
  8. customcrystallized from hexane/AcOEt

출처 및 근거

ORD 기록
ord-ac0b91e9d7d545748e842f3e428844d7
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08778944B2

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