2-(3-Chloro-6-oxo-1,6-dihydropyridazin-1-yl)acetic acid → 2-(6-Oxo-1,6-dihydropyridazin-1-yl)acetic acid

HRID 713710

반응식

HRID 713710 반응식
Cl[C:2]1[CH:7]=[CH:6][C:5](=[O:8])[N:4]([CH2:9][C:10]([OH:12])=[O:11])[N:3]=1>CO.[Pd]>[O:8]=[C:5]1[N:4]([CH2:9][C:10]([OH:12])=[O:11])[N:3]=[CH:2][CH:7]=[CH:6]1

참가 물질

4

반응물 1

HCID 51212972-(3-Chloro-6-oxo-1,6-dihydropyridazin-1-yl)acetic acid

생성물 1

HCID 14155362-(6-Oxo-1,6-dihydropyridazin-1-yl)acetic acid

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 887Methanol용매

실험 절차

[3-Chloro-6-oxopyridazin-1(6H)-yl]acetic acid (1.00 g, 5.30 mmol) in methanol (40 mL) was added 100 mg of 10% Pd/C. After the reaction mixture was stirred at ambient temperature under a H2 balloon for 1 h, the Pd was filtered off through celite. The filtrate was concentrated in vacuo and purified by reverse phase HPLC (TMC Pro-Pac C18; 0-40% 0.1% trifluoroacetic acid in acetonitrile/0.1% trifluoroacetic acid in water gradient). Removal of the volatiles in vacuo afforded the title compound as a white crystalline. 1H NMR (D2O): δ 8.06 (dd, J=3.9, 1.4 Hz, 1H), 7.56 (dd, J=9.4, 3.9 Hz, 1H), 7.12 (dd, J=9.4, 1.5 Hz, 1H), 4.95 (s, 2H). LC/MS 155.2 (M+1).

후처리

  1. filtrationthe Pd was filtered off through celite
  2. concentrationThe filtrate was concentrated in vacuo
  3. custompurified by reverse phase HPLC (TMC Pro-Pac C18; 0-40% 0.1% trifluoroacetic acid in acetonitrile/0.1% trifluoroacetic acid in water gradient)
  4. customRemoval of the volatiles in vacuo

출처 및 근거

ORD 기록
ord-4553935253964522beebfc9925035ec3
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09186354B2

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