1,2-Diaminocyclohexane, trans- → 3-[3-Fluoranyl-4-[5-Methoxy-4-Oxidanylidene-3-(2-Phenylpyrazol-3-Yl)pyridazin-1-Yl]phenyl]-1,3-Oxazolidin-2-One

HRID 1407319노트

반응식

HRID 1407319 반응식
[F:1][C:2]1[CH:7]=[C:6](I)[CH:5]=[CH:4][C:3]=1[N:9]1[CH:14]=[C:13]([O:15][CH3:16])[C:12](=[O:17])[C:11]([C:18]2[N:22]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[N:21]=[CH:20][CH:19]=2)=[N:10]1.[O:29]1[CH2:33][C:32](=O)[N:31]=[C-:30]1.N[C@@H]1CCCC[C@H]1N.[O-:43]P([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.[Cu]I.O>[F:1][C:2]1[CH:7]=[C:6]([N:31]2[CH2:32][CH2:33][O:29][C:30]2=[O:43])[CH:5]=[CH:4][C:3]=1[N:9]1[CH:14]=[C:13]([O:15][CH3:16])[C:12](=[O:17])[C:11]([C:18]2[N:22]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[N:21]=[CH:20][CH:19]=2)=[N:10]1

참가 물질

8

반응물 4

HCID 438061,2-Diaminocyclohexane, trans-HCID 62657Potassium Phosphate, TribasicHCID 532495662H-1,3-oxazol-2-id-4-oneHCID 594362141-(2-fluoro-4-iodophenyl)-5-methoxy-3-(1-phenyl-1H-pyrazol-5-yl)pyridazin-4(1H)-one

생성물 1

HCID 468489173-[3-Fluoranyl-4-[5-Methoxy-4-Oxidanylidene-3-(2-Phenylpyrazol-3-Yl)pyridazin-1-Yl]phenyl]-1,3-Oxazolidin-2-One수율 71.1%

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 962Water용매HCID 312751,4-Dioxane용매

실험 절차

A suspension of 1-(2-fluoro-4-iodophenyl)-5-methoxy-3-(1-phenyl-1H-pyrazol-5-yl)pyridazin-4(1H)-one (244 mg, 0.5 mmol), 2-oxazolidone (52.2 mg, 0.6 mmol), CuI (9.5 mg, 0.05 mmol), trans-1,2-diaminocyclohexane (0.012 mL, 0.1 mmol), and K3PO4 (212 mg, 1.0 mmol) in 1,4-dioxane (2 mL) was refluxed for 1.5 h under Ar atmosphere. The reaction mixture was poured into water and extracted with AcOEt. The extract was washed with brine, dried over MgSO4, and concentrated under reduced pressure. The residue was washed with AcOEt and recrystallized from MeOH/H2O to give the title compound (159 mg, 71% yield) as a pale yellow solid: mp 218-220° C.; 1H NMR (300 MHz, CDCl3): ppm 3.90 (3H, s), 4.03-4.08 (2H, m), 4.51-4.56 (2H, m), 6.42 (1H, t, J=9.0 Hz), 7.01 (1H, ddd, J=1.1, 2.3, 9.0 Hz), 7.30 (1H, d, J=1.9 Hz), 7.35-7.45 (5H, m), 7.66 (1H, dd, J=2.3, 13.6 Hz), 7.78 (2H, d, J=1.9 Hz). LC-MS (ESI) m/z 448 [M+H]+. Anal. Calcd for C23H18FN5O4: C, 61.74; H, 4.06; N, 15.65. Found: C, 61.48; H, 4.07; N, 15.54.

후처리

  1. temperaturewas refluxed for 1.5 h under Ar atmosphere
  2. extractionextracted with AcOEt
  3. washThe extract was washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. washThe residue was washed with AcOEt
  7. customrecrystallized from MeOH/H2O

출처 및 근거

ORD 기록
ord-9e6f9d2ee697482a85dee7e7da0a33c6
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08916566B2

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