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

HRID 451364Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 451364
[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

Komponenten

8

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

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%).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-243e824c4dc94165a39b8045c64e4b02
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08487117B2

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