Methanesulfonyl chloride → 5-[4-(2-Pyridin-2-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)-quinolin-7-yloxymethyl]-pyrrolidin-2-one

HRID 8251

Reaktionsgleichung

Reaktionsgleichung von HRID 8251
[OH:1][CH2:2][C@@H:3]1[NH:7][C:6](=[O:8])[CH2:5][CH2:4]1.CS(Cl)(=O)=O.[N:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[C:20]1[C:21]([C:28]2[C:37]3[C:32](=[CH:33][C:34](O)=[CH:35][CH:36]=3)[N:31]=[CH:30][CH:29]=2)=[C:22]2[CH2:27][CH2:26][CH2:25][N:23]2[N:24]=1>CN(C)C=O>[N:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[C:20]1[C:21]([C:28]2[C:37]3[C:32](=[CH:33][C:34]([O:1][CH2:2][CH:3]4[NH:7][C:6](=[O:8])[CH2:5][CH2:4]4)=[CH:35][CH:36]=3)[N:31]=[CH:30][CH:29]=2)=[C:22]2[CH2:27][CH2:26][CH2:25][N:23]2[N:24]=1

Komponenten

5

Edukt 3

HCID 31297Methanesulfonyl chlorideHCID 7128291(R)-(-)-5-(Hydroxymethyl)-2-pyrrolidinoneHCID 1355066154-(2-(Pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)quinolin-7-ol

Produkt 1

HCID 102242605-[4-(2-Pyridin-2-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)-quinolin-7-yloxymethyl]-pyrrolidin-2-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A solution of (R)-(−)-5-(hydroxymethyl)-2-pyrrolidinone (315 mg, 2.74 mmol) in N,N-dimethylformamide (3 mL) is treated with methansulfonyl chloride (320 mg, 2.74 mmol) and heated at 60° C. for 5 h. The reaction mixture is diluted with N,N-dimethylformamide (1 mL) and 4-(2-pyridin-2-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)-quinolin-7-ol (200 mg, 0.91 mmol) added. The mixture is stirred at 60° C. for additional 16 h, cooled to room temperature, and partitioned between ethyl acetate and water. The organic portion is washed three times with water, once with brine, dried (sodium sulfate), filtered and concentrated in vacuo. The crude residue is chromatographed on SiO2 (89% dichloromethane 10% methanol 1% concentrated ammonium hydroxide) to yield the title compound, 32 mg (8%), as a light red solid.

Aufarbeitung

  1. additionadded
  2. temperaturecooled to room temperature
  3. custompartitioned between ethyl acetate and water
  4. washThe organic portion is washed three times with water
  5. dry with materialonce with brine, dried (sodium sulfate)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude residue is chromatographed on SiO2 (89% dichloromethane 10% methanol 1% concentrated ammonium hydroxide)

Quellen und Nachweise

ORD-Eintrag
ord-ba620833bb654b8b8301ec37ef3e1997
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07087626B2

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