Nitric Acid → 5-[(2R)-2-(2,5-Difluorophenyl)-1-pyrrolidinyl]-3-nitropyrazolo[1,5-a]pyrimidine

HRID 537753Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 537753
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C@H:9]1[CH2:13][CH2:12][CH2:11][N:10]1[C:14]1[CH:19]=[CH:18][N:17]2[N:20]=[CH:21][CH:22]=[C:16]2[N:15]=1.[N+:23]([O-])([OH:25])=[O:24]>C(O)(C(F)(F)F)=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C@H:9]1[CH2:13][CH2:12][CH2:11][N:10]1[C:14]1[CH:19]=[CH:18][N:17]2[N:20]=[CH:21][C:22]([N+:23]([O-:25])=[O:24])=[C:16]2[N:15]=1

Komponenten

4

Edukt 2

HCID 944Nitric AcidHCID 67329909(R)-5-(2-(2,5-difluorophenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidine

Produkt 1

HCID 673298195-[(2R)-2-(2,5-Difluorophenyl)-1-pyrrolidinyl]-3-nitropyrazolo[1,5-a]pyrimidineAusbeute 58 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6422Trifluoroacetic acidLösungsmittel

Versuchsvorschrift

(R)-5-(2-(2,5-difluorophenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidine (3.3 g, 10.99 mmol), was dissolved in 25 mL TFA at ambient temperature to give a clear yellowish solution, then nitric acid (3.434 mL, 54.94 mmol) was added drop-wise to the solution with rapid stirring. After addition, the reaction mixture was stirred for another 15 minutes at ambient temperature, then quenched by pouring onto ice with rapid stirring. The resulting yellowish suspension was filtered, rinsed with water, then the solid was triturated with MeOH (50 mL, with brief sonication), and vacuum-filtered, giving the pure product as a fine off-white powder (2.2 g, 58% yield).

Aufarbeitung

  1. customto give a clear yellowish solution
  2. additionAfter addition
  3. customquenched
  4. additionby pouring onto ice with rapid stirring
  5. filtrationThe resulting yellowish suspension was filtered
  6. washrinsed with water
  7. customthe solid was triturated with MeOH (50 mL, with brief sonication)
  8. filtrationvacuum-filtered

Quellen und Nachweise

ORD-Eintrag
ord-a1b49a7d5b9c409fb1b20ec19e6285b8
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08865698B2

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