HCID 71766083, 화합물 → N-[4-(4-Fluoro-2-methoxy-phenyl)-pyridazin-3-yl]-3-methanesulfonyl-N-methyl-5-trifluoromethyl-benzamide

HRID 403373노트

반응식

HRID 403373 반응식
Cl[C:2]1[N:7]=[N:6][C:5]([N:8]([CH3:25])[C:9](=[O:24])[C:10]2[CH:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:13]=[C:12]([S:20]([CH3:23])(=[O:22])=[O:21])[CH:11]=2)=[C:4]([C:26]2[CH:31]=[CH:30][C:29]([F:32])=[CH:28][C:27]=2[O:33][CH3:34])[CH:3]=1>CO.C(OCC)(=O)C.[Pd]>[F:32][C:29]1[CH:30]=[CH:31][C:26]([C:4]2[CH:3]=[CH:2][N:7]=[N:6][C:5]=2[N:8]([CH3:25])[C:9](=[O:24])[C:10]2[CH:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:13]=[C:12]([S:20]([CH3:23])(=[O:22])=[O:21])[CH:11]=2)=[C:27]([O:33][CH3:34])[CH:28]=1

참가 물질

5

반응물 1

HCID 71766083HCID 71766083, 화합물

생성물 1

HCID 71744792N-[4-(4-Fluoro-2-methoxy-phenyl)-pyridazin-3-yl]-3-methanesulfonyl-N-methyl-5-trifluoromethyl-benzamide수율 27.9%

시약·촉매·용매 3

HCID 23938Palladium촉매HCID 887Methanol용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of N-[6-chloro-4-(4-fluoro-2-methoxy-phenyl)-pyridazin-3-yl]-3-methanesulfonyl-N-methyl-5-trifluoromethyl-benzamide (50 mg, 96.5 μmol, example 1) in methanol (2 mL) and ethyl acetate (2 mL) was added palladium on activated charcoal (10%, 10 mg, 96.5 μmol) under argon atmosphere. The reaction apparatus was evacuated and purged with hydrogen gas. The reaction was stirred under a hydrogen atmosphere of 1.7 bar for 8 hours. The reaction mixture was filtered over dicalite and the filtrate was concentrated under vacuum. The residue was purified by silica gel chromatography on a 10 g column using an MPLC (Flashmaster) system eluting with a gradient of n-heptane:ethyl acetate (100:0 to 0:100). The product was purified by preparative HPLC (Gemini NX column) with a gradient of methanol:water with 0.05% formic acid (80:20 to 98:2) to give the title compound as a light brown solid (13 mg, 27.9%). MS (ESI+): m/z=484.095 ([M+H]+).

후처리

  1. customThe reaction apparatus was evacuated
  2. custompurged with hydrogen gas
  3. filtrationThe reaction mixture was filtered over dicalite
  4. concentrationthe filtrate was concentrated under vacuum
  5. customThe residue was purified by silica gel chromatography on a 10 g column
  6. washeluting with a gradient of n-heptane:ethyl acetate (100:0 to 0:100)
  7. customThe product was purified by preparative HPLC (Gemini NX column) with a gradient of methanol

출처 및 근거

ORD 기록
ord-e8c9266343a54f78a9d95ab6c5484028
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08748434B2

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