Oxalyl chloride → HCID 25256384, Verbindung

HRID 219919

Reaktionsgleichung

Reaktionsgleichung von HRID 219919
C(Cl)(=O)C(Cl)=O.[CH3:7][CH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][N:9]1[C:14]1[CH:22]=[CH:21][C:17]([C:18](O)=[O:19])=[CH:16][C:15]=1[C:23]([F:26])([F:25])[F:24].[C:27]([C:29]1[CH:34]=[CH:33][C:32]([S:35]([NH2:38])(=[O:37])=[O:36])=[CH:31][CH:30]=1)#[N:28].CC[N:41](C(C)C)C(C)C>C(Cl)Cl.C1COCC1.CN(C=O)C>[CH3:7][CH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][N:9]1[C:14]1[CH:22]=[CH:21][C:17]([C:18]2[O:19][N:41]=[C:27]([C:29]3[CH:30]=[CH:31][C:32]([S:35]([NH2:38])(=[O:37])=[O:36])=[CH:33][CH:34]=3)[N:28]=2)=[CH:16][C:15]=1[C:23]([F:26])([F:24])[F:25]

Komponenten

8

Edukt 4

HCID 65578Oxalyl chlorideHCID 76566p-CyanobenzenesulphonamideHCID 81531DiisopropylethylamineHCID 594956554-(2-Methylpiperidin-1-YL)-3-(trifluoromethyl)benzoic acid

Produkt 1

HCID 25256384HCID 25256384, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Oxalyl chloride (190 mg; 1.5 mmol) was added to a suspension of Intermediate 15 (144 mg; 0.5 mmol) and DMF (catalytic amount) in DCM (2 mL) and the reaction mixture was stirred at RT for 1 hour. After concentration to dryness, the residue was taken up in THF (2 mL) and added to a solution of 4-(aminosulfonyl)-N′-hydroxybenzenecarboximidamide, prepared as described in WO 2006/013104 A1 from 4-cyanobenzene-1-sulfonamide (ABCR; CD10716), (108 mg; 05 mmol, 1 eq.) and DIEA (194 mg; 1.5 mmol) in THF (1 mL). The reaction mixture was then stirred at 150° C. for 30 minutes in the microwave. After cooling, the mixture was filtered through a SPE-NH2 column, which was further washed with THF. After concentration in vacuo, the residue was purified by recrystallisation from DCM/n-pentane, affording the title compound as a white solid. LC/MS (Method A): 467.3 (M+H)+. HPLC (Method A) Rt 5.59 min (purity 99.3%).

Aufarbeitung

  1. concentrationAfter concentration to dryness
  2. additionadded to a solution of 4-(aminosulfonyl)-N′-hydroxybenzenecarboximidamide
  3. customprepared
  4. stirringThe reaction mixture was then stirred at 150° C. for 30 minutes in the microwave
  5. temperatureAfter cooling
  6. filtrationthe mixture was filtered through a SPE-NH2 column, which
  7. washwas further washed with THF
  8. concentrationAfter concentration in vacuo
  9. customthe residue was purified by recrystallisation from DCM/n-pentane

Quellen und Nachweise

ORD-Eintrag
ord-5876900a117842c7b97baa345b431383
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08202865B2

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