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

HRID 403373ノート

反応式

HRID 403373 の反応式
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

参加物

5

反応物 1

HCID 71766083HCID 71766083、化合物

生成物 1

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

試薬・触媒・溶媒 3

HCID 23938Palladium触媒HCID 887Methanol溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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]+).

後処理

  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

出典と根拠

ORDレコード
ord-e8c9266343a54f78a9d95ab6c5484028
出典データセット
uspto-grants-2014_06
特許番号
US08748434B2

反応ノート

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