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1,1'-Carbonyldiimidazole → (S)-N-(3-chloropropyl)-5-(4-(5-fluoro-2-methoxypyridin-3-yl)-2-oxooxazolidin-3-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide

HRID 1426960
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1426960
[Cl:1][CH2:2][CH2:3][CH2:4][NH:5][C:6]([C:8]1[CH:9]=[N:10][N:11]2[CH:16]=[CH:15][C:14]([NH:17][C@@H:18]([C:21]3[C:22]([O:28][CH3:29])=[N:23][CH:24]=[C:25]([F:27])[CH:26]=3)[CH2:19][OH:20])=[N:13][C:12]=12)=[O:7].C1N=CN([C:35](N2C=NC=C2)=[O:36])C=1>C(#N)C>[Cl:1][CH2:2][CH2:3][CH2:4][NH:5][C:6]([C:8]1[CH:9]=[N:10][N:11]2[CH:16]=[CH:15][C:14]([N:17]3[C@@H:18]([C:21]4[C:22]([O:28][CH3:29])=[N:23][CH:24]=[C:25]([F:27])[CH:26]=4)[CH2:19][O:20][C:35]3=[O:36])=[N:13][C:12]=12)=[O:7]
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Komponenten

4

Edukt 2

HCID 682631,1'-CarbonyldiimidazoleHCID 86691744(S)-N-(3-chloropropyl)-5-(1-(5-fluoro-2-methoxypyridin-3-yl)-2-hydroxyethylamino)pyrazolo[1,5-a]pyrimidine-3-carboxamide

Produkt 1

HCID 86691745(S)-N-(3-chloropropyl)-5-(4-(5-fluoro-2-methoxypyridin-3-yl)-2-oxooxazolidin-3-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamideAusbeute 58,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342Acetonitrile
Lösungsmittel

Versuchsvorschrift

To a solution of (S)-N-(3-chloropropyl)-5-(1-(5-fluoro-2-methoxypyridin-3-yl)-2-hydroxyethylamino)pyrazolo[1,5-a]pyrimidine-3-carboxamide (60 mg, 0.14 mmol) in ACN (2 mL) was added CDI (35 mg, 0.21 mmol). The solution was stirred at ambient temperature for 16 hours then partitioned between saturated NH4Cl solution (20 mL) and EtOAc (10 mL) and the layers separated. The aqueous layer was extracted with EtOAc (2×10 mL) and the combined organic phases were washed with brine (10 mL), dried over Na2SO4, filtered and concentrated. The residue was purified by flash column chromatography eluting with 1% MeOH/DCM to afford (S)-N-(3-chloropropyl)-5-(4-(5-fluoro-2-methoxypyridin-3-yl)-2-oxooxazolidin-3-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide (37 mg, 58% yield) as a white solid. MS (apci) m/z=449.0 (M+H).

Aufarbeitung

  1. customthen partitioned between saturated NH4Cl solution (20 mL) and EtOAc (10 mL)
  2. customthe layers separated
  3. extractionThe aqueous layer was extracted with EtOAc (2×10 mL)
  4. washthe combined organic phases were washed with brine (10 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by flash column chromatography
  9. washeluting with 1% MeOH/DCM

Quellen und Nachweise

ORD-Eintrag
ord-522a4497e71e47b189628d343a5195b5
Quelldatensatz
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08933084B2

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