o-Toluenesulfonyl chloride → 7-(3-Chloro-propylsulfanyl)-4-(2-pyridin-2-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)-quinoline

HRID 8261

Reaktionsgleichung

Reaktionsgleichung von HRID 8261
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[C:8]([C:15]2[C:24]3[C:19](=[CH:20][C:21]([S:25][CH2:26][CH2:27][CH2:28]O)=[CH:22][CH:23]=3)[N:18]=[CH:17][CH:16]=2)=[C:9]2[CH2:14][CH2:13][CH2:12][N:10]2[N:11]=1.C1(C)C(S([Cl:39])(=O)=O)=CC=CC=1.C(=O)(O)[O-].[Na+]>N1C=CC=CC=1>[Cl:39][CH2:28][CH2:27][CH2:26][S:25][C:21]1[CH:20]=[C:19]2[C:24]([C:15]([C:8]3[C:7]([C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=4)=[N:11][N:10]4[CH2:12][CH2:13][CH2:14][C:9]=34)=[CH:16][CH:17]=[N:18]2)=[CH:23][CH:22]=1

Komponenten

5

Edukt 3

HCID 8623o-Toluenesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 219925373-[4-(2-pyridin-2-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)-quinolin-7-ylsulfanyl]-propan-1-ol

Produkt 1

HCID 101591567-(3-Chloro-propylsulfanyl)-4-(2-pyridin-2-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)-quinoline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

To a solution of Preparation #21, 3-[4-(2-pyridin-2-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)-quinolin-7-ylsulfanyl]-propan-1-ol (25.0 mg, 0.062 mmol) in dry pyridine (0.1 mL) is added toluene sulfonyl chloride (60.0 mg, 0.31 mmol) and the resulting mixture stirred at room temperature for 72 h. Saturated sodium bicarbonate solution is added and the resulting solution extracted with ethyl acetate. The organic layer is washed with brine, dried (sodium sulfate), filtered, and concentrated in vacuo. Purification of the residue on SiO2 (5% to 10% methanol in dichloromethane) gives the desired product, 11.2 mg (43%). MS ES+ m/e 421.1 (M+1).

Aufarbeitung

  1. extractionthe resulting solution extracted with ethyl acetate
  2. washThe organic layer is washed with brine
  3. dry with materialdried (sodium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification of the residue on SiO2 (5% to 10% methanol in dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-cb9b6c262d904ba286a664c696baaedc
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07087626B2

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