Cyclopropanecarbonyl chloride → N-(7-(cyclopropylamino)-3-formylpyrazolo[1,5-a]pyrimidin-5-yl)cyclopropanecarboxamide

HRID 624702Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 624702
[NH2:1][C:2]1[CH:7]=[C:6]([NH:8][CH:9]2[CH2:11][CH2:10]2)[N:5]2[N:12]=[CH:13][C:14]([CH:15]=[O:16])=[C:4]2[N:3]=1.[CH:17]1([C:20](Cl)=[O:21])[CH2:19][CH2:18]1.CCN(C(C)C)C(C)C>O1CCCC1>[CH:9]1([NH:8][C:6]2[N:5]3[N:12]=[CH:13][C:14]([CH:15]=[O:16])=[C:4]3[N:3]=[C:2]([NH:1][C:20]([CH:17]3[CH2:19][CH2:18]3)=[O:21])[CH:7]=2)[CH2:11][CH2:10]1

Komponenten

5

Edukt 3

HCID 77637Cyclopropanecarbonyl chlorideHCID 81531DiisopropylethylamineHCID 583137635-Amino-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidine-3-carbaldehyde

Produkt 1

HCID 86654652N-(7-(cyclopropylamino)-3-formylpyrazolo[1,5-a]pyrimidin-5-yl)cyclopropanecarboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To 5-amino-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidine-3-carbaldehyde (step b) (58 mg, 0.266 mmol) in 1.0 mL tetrahydrofuran was added cyclopropane carbonyl chloride (38 ul, 0.419 mmol) and DIPEA (39.0 ul). The reaction mixture was heated at 60° C. for one hour. The reaction was partitioned between ethyl acetate and water, the organic layer was dried under sodium sulfate concentrated on high vac to yield N-(7-(cyclopropylamino)-3-formylpyrazolo[1,5-a]pyrimidin-5-yl)cyclopropanecarboxamide. The crude product was taken to next step without further purification. LCMS (M+1=286)

Aufarbeitung

  1. customThe reaction was partitioned between ethyl acetate and water
  2. customthe organic layer was dried under sodium sulfate
  3. concentrationconcentrated on high vac

Quellen und Nachweise

ORD-Eintrag
ord-2126012f42354e2ebc0738c1a1a938b9
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09303033B2

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