Triethylamine → 6-(phenylsulfonamido)-N-(tetrahydro-2H-pyran-2-yloxy)quinoline-3-carboxamide

HRID 1894964Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1894964
[C:1]1([S:7]([NH:10][C:11]2[CH:12]=[C:13]3[C:18](=[CH:19][CH:20]=2)[N:17]=[CH:16][C:15]([C:21](O)=[O:22])=[CH:14]3)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.F[P-](F)(F)(F)(F)F.CN(C)C(F)=[N+](C)C.[O:46]1[CH2:51][CH2:50][CH2:49][CH2:48][CH:47]1[O:52][NH2:53]>CN(C)C=O.O>[C:1]1([S:7]([NH:10][C:11]2[CH:12]=[C:13]3[C:18](=[CH:19][CH:20]=2)[N:17]=[CH:16][C:15]([C:21]([NH:53][O:52][CH:47]2[CH2:48][CH2:49][CH2:50][CH2:51][O:46]2)=[O:22])=[CH:14]3)(=[O:8])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 2774761Tetramethylfluoroformamidinium hexafluorophosphateHCID 5142091O-(Tetrahydropyran-2-yl)hydroxylamineHCID 670023616-[(Phenylsulfonyl)amino]quinoline-3-carboxylic acid

Produkt 1

HCID 866595026-(phenylsulfonamido)-N-(tetrahydro-2H-pyran-2-yloxy)quinoline-3-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

6-[(Phenylsulfonyl)amino]quinoline-3-carboxylic acid (0.11 g, 0.335 mmol) was dissolved in N,N-dimethylformamide (2.5 mL) and triethylamine (0.14 mL, 1 mmol) was added. Tetramethylfluoroformamidinium hexafluorophosphate (0.106 g, 0.402 mmol) was added and the reaction mixture was allowed to stir at room temperature for 15 min. Then O-(tetrahydropyran-2-yl)hydroxylamine (0.0471 g, 0.402 mmol) was added and the reaction was stirred at room temperature overnight. The reaction mixture was poured into water and extracted with ethyl acetate three times. The combined extracts were washed with water, brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude residue was purified by silica gel chromatography (0-10% MeOH in methylene chloride gradient with 0.1% formic acid) to afford the product (Int-13, 0.027 g, 18%). LC-MS: (AA) ES+ 428.

Aufarbeitung

  1. stirringthe reaction was stirred at room temperature overnight
  2. extractionextracted with ethyl acetate three times
  3. washThe combined extracts were washed with water, brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude residue was purified by silica gel chromatography (0-10% MeOH in methylene chloride gradient with 0.1% formic acid)
  8. customto afford the product (Int-13, 0.027 g, 18%)

Quellen und Nachweise

ORD-Eintrag
ord-834e8e84bc044ce78d4d1dae591de334
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08513421B2

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