Ammonia → 1-{3-[3-(3,5-difluorophenyl)-6-oxo-6H-pyridazin-1-yl-methyl]phenyl}-3-methyl-6H-pyridazin-6-one

HRID 1408388

반응식

HRID 1408388 반응식
C(=O)([O-])[O-].[K+].[K+].OC1C=CC=C2C=1N=CC=C2.[F:18][C:19]1[CH:20]=[C:21]([C:26]2[CH:27]=[CH:28][C:29](=[O:40])[N:30]([CH2:32][C:33]3[CH:38]=[CH:37][CH:36]=[C:35](I)[CH:34]=3)[N:31]=2)[CH:22]=[C:23]([F:25])[CH:24]=1.[CH3:41][C:42]1[CH:43]=[CH:44][C:45](=[O:48])[NH:46][N:47]=1.N>CN(C=O)C.[Cu]I.C(OCC)(=O)C>[F:18][C:19]1[CH:20]=[C:21]([C:26]2[CH:27]=[CH:28][C:29](=[O:40])[N:30]([CH2:32][C:33]3[CH:34]=[C:35]([N:46]4[C:45](=[O:48])[CH:44]=[CH:43][C:42]([CH3:41])=[N:47]4)[CH:36]=[CH:37][CH:38]=3)[N:31]=2)[CH:22]=[C:23]([F:25])[CH:24]=1

참가 물질

9

반응물 5

HCID 222AmmoniaHCID 19238-HydroxyquinolineHCID 11430Potassium CarbonateHCID 833466-methylpyridazin-3(2H)-oneHCID 594848336-(3,5-difluorophenyl)-2-(3-iodobenzyl)-2H-pyridazin-3-one

생성물 1

HCID 594848471-{3-[3-(3,5-difluorophenyl)-6-oxo-6H-pyridazin-1-yl-methyl]phenyl}-3-methyl-6H-pyridazin-6-one

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

반응 조건

온도
120 °C

실험 절차

3.2 14.3 mg (0.08 mmol) of copper(I) iodide, 76 mg (0.55 mmol) of potassium carbonate and 11 mg (0.08 mmol) of 8-hydroxyquinoline are added to a solution of 212 mg (0.50 mmol) of 6-(3,5-difluorophenyl)-2-(3-iodobenzyl)-2H-pyridazin-3-one and 55.1 mg (0.5 mmol) of 6-methylpyridazin-3(2H)-one in 2 ml of DMF, and the mixture is heated at 120° C. for 24 hours. The reaction mixture is allowed to cool, and 10% aqueous ammonia solution and ethyl acetate are added. The resultant precipitate is filtered off with suction, washed with water and dried. The residue is boiled in ethyl acetate, filtered off with suction and washed with ethyl acetate. The residue is dried in vacuo: 1-{3-[3-(3,5-difluorophenyl)-6-oxo-6H-pyridazin-1-ylmethyl]phenyl}-3-methyl-6H-pyridazin-6-one (“A8”) as brownish crystals; ESI 407.

후처리

  1. temperatureto cool
  2. filtrationThe resultant precipitate is filtered off with suction
  3. washwashed with water
  4. customdried
  5. filtrationfiltered off with suction
  6. washwashed with ethyl acetate
  7. customThe residue is dried in vacuo

출처 및 근거

ORD 기록
ord-dc5bc57d95c44ce3aef677097a96c5c1
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08921357B2

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