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4-(Trifluoromethyl)benzenesulfonyl chloride → N-[4-(1,3-benzodioxol-5-yl)-3-methoxy-1-methyl-1H-pyrazol-5-yl]-4-(trifluoromethyl)benzenesulfonamide

HRID 1062754
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1062754
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:8]=[CH:7][C:6]([S:9](Cl)(=[O:11])=[O:10])=[CH:5][CH:4]=1.[NH2:15][C:16]1[N:20]([CH3:21])[N:19]=[C:18]([O:22][CH3:23])[C:17]=1[C:24]1[CH:32]=[CH:31][C:27]2[O:28][CH2:29][O:30][C:26]=2[CH:25]=1>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[O:28]1[C:27]2[CH:31]=[CH:32][C:24]([C:17]3[C:18]([O:22][CH3:23])=[N:19][N:20]([CH3:21])[C:16]=3[NH:15][S:9]([C:6]3[CH:7]=[CH:8][C:3]([C:2]([F:14])([F:13])[F:1])=[CH:4][CH:5]=3)(=[O:11])=[O:10])=[CH:25][C:26]=2[O:30][CH2:29]1
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Komponenten

5

Edukt 2

HCID 27773994-(Trifluoromethyl)benzenesulfonyl chlorideHCID 222819435-amino-4-(1,3-benzodioxol-5-yl)-3-methoxy-1-methyl-1H-pyrazole

Produkt 1

HCID 22281890N-[4-(1,3-benzodioxol-5-yl)-3-methoxy-1-methyl-1H-pyrazol-5-yl]-4-(trifluoromethyl)benzenesulfonamideAusbeute 0,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysator
HCID 1049
Pyridine
Lösungsmittel
2×

Versuchsvorschrift

To a solution of 4-dimethylaminopyridine in anhydrous pyridine at 0° C. under an atmosphere of nitrogen was added 4-(trifluoromethyl)benzenesulfonyl chloride (148 mg) in pyridine (1.5 ml). After 10 min the reaction was treated with 5-amino-4-(1,3-benzodioxol-5-yl)-3-methoxy-1-methyl-1H-pyrazole (Preparation 43) (100 mg) and the reaction was allowed to warm to room temperature and stirred for 12 h. The reaction was concentrated under reduced pressure, the residue treated with 1.0M aqueous citric acid (100 ml) and extracted with dichloromethane (3×50 ml). The combined organic fractions were dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by HPLC (eluent of 55% water in acetonitrile to 30% water in acetonitrile over 8 mins, then 30% water in acetonitrile for 13 mins. Phenomenex Magellen™ 150 mm×21.5 mm column, 40° C.) to yield the title compound as an off-white solid (1 mg).

Aufarbeitung

  1. concentrationThe reaction was concentrated under reduced pressure
  2. additionthe residue treated with 1.0M aqueous citric acid (100 ml)
  3. extractionextracted with dichloromethane (3×50 ml)
  4. dry with materialThe combined organic fractions were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by HPLC (eluent of 55% water in acetonitrile to 30% water in acetonitrile over 8 mins
  8. wait30% water in acetonitrile for 13 mins

Quellen und Nachweise

ORD-Eintrag
ord-15cfab0ba89242ca8852b5e2877410d3
Quelldatensatz
uspto-grants-2005_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06962923B2

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