Oxalyl chloride → 1,4-dimethyl-5-(2-trifluoromethyl-phenyl)-1H-pyrrole-3-carboxylic acid (4-methanesulfonyl-phenyl)-amide

HRID 383751ノート

反応式

HRID 383751 の反応式
[CH3:1][N:2]1[C:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[C:13]([F:16])([F:15])[F:14])=[C:5]([CH3:17])[C:4]([C:18]([OH:20])=O)=[CH:3]1.C(Cl)(=O)C(Cl)=O.[CH3:27][S:28]([C:31]1[CH:37]=[CH:36][C:34]([NH2:35])=[CH:33][CH:32]=1)(=[O:30])=[O:29].CCN(C(C)C)C(C)C>C(Cl)Cl.C1COCC1>[CH3:27][S:28]([C:31]1[CH:37]=[CH:36][C:34]([NH:35][C:18]([C:4]2[C:5]([CH3:17])=[C:6]([C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[C:13]([F:16])([F:14])[F:15])[N:2]([CH3:1])[CH:3]=2)=[O:20])=[CH:33][CH:32]=1)(=[O:29])=[O:30]

参加物

7

反応物 4

HCID 65578Oxalyl chlorideHCID 796174-(Methylsulfonyl)anilineHCID 81531DiisopropylethylamineHCID 67252161HCID 67252161、化合物

生成物 1

HCID 250520241,4-dimethyl-5-(2-trifluoromethyl-phenyl)-1H-pyrrole-3-carboxylic acid (4-methanesulfonyl-phenyl)-amide収率 28%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 1,4-dimethyl-5-(2-trifluoromethyl-phenyl)-1H-pyrrole-3-carboxylic acid (56 mg, 0.20 mmol) in DCM (4 mL) was added oxalyl chloride (22 pt, 0.25 mmol). After stirring 30 min, solvent was removed in vacuo to give an oil, which was re-dissolved in anhyd THF (4 mL). To this solution were added 4-methanesulfonyl-aniline (68 mg, 0.40 mmol) and DIEA (140 μL, 0.8 mmol) and the mixture was stirred at 60° C. overnight. After cooling, solvent was removed in vacuo to give a crude residue, which was purified by column chromatography on silica gel, eluted with EtOAc-hexane (0:100 to 25:75) to give the title compound (24 mg, 28%). 1H-NMR (CDCl3): δ 7.89-7.91 (m, 2H), 7.80 (m, 3H), 7.57-7.66 (m, 3H), 7.33 (d, 1H), 7.30 (s, 1H), 3.32 (s, 3H), 3.05 (s, 3H), 2.12 (s, 3H). MS (ES): 437 (MH+). E. In a manner similar to that described for Example 16D, the following compounds were prepared from the appropriate anilines:

後処理

  1. customsolvent was removed in vacuo
  2. customto give an oil, which
  3. stirringthe mixture was stirred at 60° C. overnight
  4. temperatureAfter cooling
  5. customsolvent was removed in vacuo
  6. customto give a crude residue, which
  7. customwas purified by column chromatography on silica gel
  8. washeluted with EtOAc-hexane (0:100 to 25:75)

出典と根拠

ORDレコード
ord-b32b29c02dbc4c53a8b8c890aceac7ea
出典データセット
uspto-grants-2013_02
特許番号
US08367667B2

反応ノート

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