Oxalyl chloride → 5-[4-chloro-2-(trifluoromethyl)phenyl]-4-methyl-N-[4-(methylsulfonyl)phenyl]-1H-pyrrole-3-carboxamide

HRID 451364ノート

反応式

HRID 451364 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:12][CH:11]=[C:10]([C:13]([OH:15])=O)[C:9]=2[CH3:16])=[C:4]([C:17]([F:20])([F:19])[F:18])[CH:3]=1.C(Cl)(=O)C(Cl)=O.Cl.[CH3:28][S:29]([C:32]1[CH:38]=[CH:37][C:35]([NH2:36])=[CH:34][CH:33]=1)(=[O:31])=[O:30].CCN(C(C)C)C(C)C>ClCCl.C(OCC)(=O)C.C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:12][CH:11]=[C:10]([C:13]([NH:36][C:35]3[CH:34]=[CH:33][C:32]([S:29]([CH3:28])(=[O:31])=[O:30])=[CH:38][CH:37]=3)=[O:15])[C:9]=2[CH3:16])=[C:4]([C:17]([F:20])([F:19])[F:18])[CH:3]=1

参加物

8

反応物 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 27351804-(Methylsulfonyl)aniline hydrochlorideHCID 584885165-[4-chloro-2-(trifluoromethyl)phenyl]-4-methyl-1H-pyrrole-3-carboxylic acid

生成物 1

HCID 584885155-[4-chloro-2-(trifluoromethyl)phenyl]-4-methyl-N-[4-(methylsulfonyl)phenyl]-1H-pyrrole-3-carboxamide収率 44%

試薬・触媒・溶媒 3

HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a suspension of 5-[4-chloro-2-(trifluoromethyl)phenyl]-4-methyl-1H-pyrrole-3-carboxylic acid (0.36 g, 1.2 mmol) in dichloromethane (5.0 ml) was added oxalyl chloride (0.3 ml, 3.5 mmol). The mixture was stirred at room temperature for 1.0 h, after which time the solvent was removed on a rotary evaporator. To this brown residue was added THF (5.0 ml), 4-(methanesulfonyl)aniline hydrochloride (0.3 g, 1.4 mmol), and DIEA (0.81 ml, 4.8 mmol). The solution was stirred at room temperature for 3.0 h. The reaction mixture was diluted with ethyl acetate and washed with water and brine, then dried over sodium sulfate and concentrated on a rotary evaporator. To the residue was added IPE and triturated. The solid was filtered to give the title compound (0.24 g, 44%).

後処理

  1. customafter which time the solvent was removed on a rotary evaporator
  2. stirringThe solution was stirred at room temperature for 3.0 h
  3. washwashed with water and brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated on a rotary evaporator
  6. additionTo the residue was added IPE
  7. customtriturated
  8. filtrationThe solid was filtered

出典と根拠

ORDレコード
ord-243e824c4dc94165a39b8045c64e4b02
出典データセット
uspto-grants-2013_07
特許番号
US08487117B2

反応ノート

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