Morpholine → (R)-N-(5-(2-(3-fluorophenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidin-3-yl)morpholine-4-carboxamide

HRID 2275343

Reaktionsgleichung

Reaktionsgleichung von HRID 2275343
[F:1][C:2]1[CH:3]=[C:4]([C@H:8]2[CH2:12][CH2:11][CH2:10][N:9]2[C:13]2[CH:18]=[CH:17][N:16]3[N:19]=[CH:20][C:21]([NH2:22])=[C:15]3[N:14]=2)[CH:5]=[CH:6][CH:7]=1.C1N=CN([C:28]([N:30]2[CH:34]=N[CH:32]=[CH:31]2)=[O:29])C=1.N1CC[O:38][CH2:37]C1>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([C@H:8]2[CH2:12][CH2:11][CH2:10][N:9]2[C:13]2[CH:18]=[CH:17][N:16]3[N:19]=[CH:20][C:21]([NH:22][C:28]([N:30]4[CH2:31][CH2:32][O:38][CH2:37][CH2:34]4)=[O:29])=[C:15]3[N:14]=2)[CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 8083MorpholineHCID 682631,1'-CarbonyldiimidazoleHCID 67329531(R)-5-(2-(3-fluorophenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidin-3-amine

Produkt 1

HCID 58386309(R)-N-(5-(2-(3-fluorophenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidin-3-yl)morpholine-4-carboxamideAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a DCM (0.8 mL) solution of (R)-5-(2-(3-fluorophenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidin-3-amine (50 mg, 0.17 mmol) was added CDI (41 mg, 0.25 mmol) at ambient temperature in one portion. After stirring two hours, morpholine (22 mg, 0.25 mmol) was added in one portion. The reaction was stirred for 5 minutes before it was concentrated and directly purified by reverse-phase column chromatography, eluting with 5 to 54% acetonitrile/water to yield the final product as a yellowish foamy powder (69 mg, 100% yield). MS (apci) m/z=411.2 (M+H).

Aufarbeitung

  1. stirringThe reaction was stirred for 5 minutes before it
  2. concentrationwas concentrated
  3. customdirectly purified by reverse-phase column chromatography
  4. washeluting with 5 to 54% acetonitrile/water

Quellen und Nachweise

ORD-Eintrag
ord-ca583bae4b8945a89c46b23cb8e314ab
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09127013B2

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