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Hydrazine → methyl 5-((R)-2-(1-((R)-3-amino-2-methylpropyl)-5-fluoro-2-oxo-1,2-dihydropyridin-3-yl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidine-3-carboxylate

HRID 1426973
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1426973
O=C1C2C(=CC=CC=2)C(=O)[N:3]1[CH2:12][C@@H:13]([CH3:41])[CH2:14][N:15]1[CH:20]=[C:19]([F:21])[CH:18]=[C:17]([C@H:22]2[CH2:26][CH2:25][CH2:24][N:23]2[C:27]2[CH:32]=[CH:31][N:30]3[N:33]=[CH:34][C:35]([C:36]([O:38][CH3:39])=[O:37])=[C:29]3[N:28]=2)[C:16]1=[O:40].NN>CO.C1COCC1>[NH2:3][CH2:12][C@@H:13]([CH3:41])[CH2:14][N:15]1[CH:20]=[C:19]([F:21])[CH:18]=[C:17]([C@H:22]2[CH2:26][CH2:25][CH2:24][N:23]2[C:27]2[CH:32]=[CH:31][N:30]3[N:33]=[CH:34][C:35]([C:36]([O:38][CH3:39])=[O:37])=[C:29]3[N:28]=2)[C:16]1=[O:40]
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Komponenten

4

Edukt 2

HCID 9321HydrazineHCID 67471119methyl 5-((R)-2-(1-((S)-3-(1,3-dioxoisoindolin-2-yl)-2-methylpropyl)-5-fluoro-2-oxo-1,2-dihydropyridin-3-yl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidine-3-carboxylate

Produkt 1

HCID 67471049methyl 5-((R)-2-(1-((R)-3-amino-2-methylpropyl)-5-fluoro-2-oxo-1,2-dihydropyridin-3-yl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidine-3-carboxylateAusbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21899815
MeOH tetrahydrofuran
Lösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a solution of methyl 5-((R)-2-(1-((S)-3-(1,3-dioxoisoindolin-2-yl)-2-methylpropyl)-5-fluoro-2-oxo-1,2-dihydropyridin-3-yl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidine-3-carboxylate (110 mg, 0.197 mmol) in MeOH/THF (3 mL/3 mL) was added hydrazine (31.6 mg, 0.985 mmol). The reaction was stirred for 14 hours at 50° C. After cooling, the reaction mixture was concentrated and the resulting residue was diluted with EtOAc (20 mL) and washed with saturated aqueous NaHCO3 (5 mL), water (2×5 mL) and brine (5 mL). The organic layer was dried with Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by silica column chromatography, eluting with EtOAc/MeOH/NH4OH 10:1:0.1 to give the desired product (65 mg, 77% yield). MS (apci) m/z=429.2 (M+H).

Aufarbeitung

  1. temperatureAfter cooling
  2. concentrationthe reaction mixture was concentrated
  3. additionthe resulting residue was diluted with EtOAc (20 mL)
  4. washwashed with saturated aqueous NaHCO3 (5 mL), water (2×5 mL) and brine (5 mL)
  5. dry with materialThe organic layer was dried with Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica column chromatography
  9. washeluting with EtOAc/MeOH/NH4OH 10:1:0.1

Quellen und Nachweise

ORD-Eintrag
ord-d8d2f22ec6fb43778b5cf480f3a71b0d
Quelldatensatz
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08933084B2

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