Pyridine → 6-{4-[2-(Trifluoromethyl)phenoxy]piperidin-1-yl}pyridazine-3-carbonitrile

HRID 1714875노트

반응식

HRID 1714875 반응식
[F:1][C:2]([F:26])([F:25])[C:3]1[CH:24]=[CH:23][CH:22]=[CH:21][C:4]=1[O:5][CH:6]1[CH2:11][CH2:10][N:9]([C:12]2[N:17]=[N:16][C:15]([C:18]([NH2:20])=O)=[CH:14][CH:13]=2)[CH2:8][CH2:7]1.N1C=CC=CC=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O.C([O-])(O)=O.[Na+]>O1CCOCC1.C(OCC)(=O)C>[F:25][C:2]([F:1])([F:26])[C:3]1[CH:24]=[CH:23][CH:22]=[CH:21][C:4]=1[O:5][CH:6]1[CH2:11][CH2:10][N:9]([C:12]2[N:17]=[N:16][C:15]([C:18]#[N:20])=[CH:14][CH:13]=2)[CH2:8][CH2:7]1

참가 물질

7

반응물 4

HCID 1049PyridineHCID 9845Trifluoroacetic anhydrideHCID 516892Sodium BicarbonateHCID 462254256-(4-(2-(Trifluoromethyl)phenoxy)piperidin-1-yl)pyridazine-3-carboxamide

생성물 1

HCID 685040226-{4-[2-(Trifluoromethyl)phenoxy]piperidin-1-yl}pyridazine-3-carbonitrile

시약·촉매·용매 2

HCID 8857Ethyl Acetate용매HCID 312751,4-Dioxane용매

실험 절차

To a solution of 6-{4-[2-(trifluoromethyl)phenoxy]piperidin-1-yl}pyridazine-3-carboxamide (1.35 g, 3.69 mmol) and pyridine (1.49 mL, 18.43 mmol) in 1,4-dioxane (30 mL) at 0° C. was added trifluoroacetic anhydride (1.04 mL, 7.37 mmol). The mixture was warmed to room temperature and stirred for 2 days. Aqueous saturated NaHCO3 and ethyl acetate were added. The layers were separated and the aqueous phase was extracted four times with ethyl acetate. The combined organic extracts were washed with brine, dried (NaSO4) and concentrated. Purification by silica gel chromatography (gradient 60% ethyl acetate:hexanes to 100% ethyl acetate) provided the title compound. 1H NMR (acetone-d6) δ 7.75 (1H, d, J=9.6 Hz), 7.68-7.62 (2H, m), 7.37 (2H, dd, J=8.4, 13.9 Hz), 7.13 (1H, t, J=7.6 Hz), 5.08-5.04 (1H, m), 4.06-4.02 (4H, m), 2.20-2.14 (2H, m), 2.00-1.94 (2H, m).

후처리

  1. customThe layers were separated
  2. extractionthe aqueous phase was extracted four times with ethyl acetate
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried (NaSO4)
  5. concentrationconcentrated
  6. customPurification by silica gel chromatography (gradient 60% ethyl acetate:hexanes to 100% ethyl acetate)

출처 및 근거

ORD 기록
ord-4641f3063dfc46069c2acffaf8e75f3b
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07799787B2

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