p-(Trifluoromethoxy)benzenesulphonyl chloride → N-[7-(4-Trifluoromethoxy-benzenesulfonylamino)-3,4-dihydro-2H-pyrano[3,2-b]pyridin-3-yl]-propionamide

HRID 870370

Reaktionsgleichung

Reaktionsgleichung von HRID 870370
[NH2:1][C:2]1[CH:3]=[C:4]2[O:11][CH2:10][CH:9]([NH:12][C:13](=[O:16])[CH2:14][CH3:15])[CH2:8][C:5]2=[N:6][CH:7]=1.[F:17][C:18]([F:31])([F:30])[O:19][C:20]1[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=1>C(Cl)Cl.N1C=CC=CC=1>[F:31][C:18]([F:17])([F:30])[O:19][C:20]1[CH:25]=[CH:24][C:23]([S:26]([NH:1][C:2]2[CH:3]=[C:4]3[O:11][CH2:10][CH:9]([NH:12][C:13](=[O:16])[CH2:14][CH3:15])[CH2:8][C:5]3=[N:6][CH:7]=2)(=[O:28])=[O:27])=[CH:22][CH:21]=1

Komponenten

4

Edukt 2

HCID 523102p-(Trifluoromethoxy)benzenesulphonyl chlorideHCID 68912527N-(7-amino-3,4-dihydro-2H-pyrano[3,2-b]pyridin-3-yl)propionamide

Produkt 1

HCID 68914768N-[7-(4-Trifluoromethoxy-benzenesulfonylamino)-3,4-dihydro-2H-pyrano[3,2-b]pyridin-3-yl]-propionamideAusbeute 47 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21875418Pyridine methylene chlorideLösungsmittel

Versuchsvorschrift

A portion of the raw N-(7-amino-3,4-dihydro-2H-pyrano[3,2-b]pyridin-3-yl)propionamide (100 mg, 0.45 mmol) was dissolved in CH2Cl2/pyridine 9/1 (20 ml) and 4-(trifluoromethoxy)benzenesulfonyl chloride (100 μl, 0.58 mmol) was added dropwise. After stirring at room temperature over night, the reaction mixture was concentrated and the purification of the residue by chromatography on silica gel (CH2Cl2:CH3OH, 97:3) gave the title compound (94 mg, 47% for steps 31.4 and 31.5) as a gum.

Aufarbeitung

  1. concentrationthe reaction mixture was concentrated
  2. customthe purification of the residue by chromatography on silica gel (CH2Cl2:CH3OH, 97:3)

Quellen und Nachweise

ORD-Eintrag
ord-43abe4bff7e74e6b96acf01df0990428
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08969552B2

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