2-Fluorobenzoyl chloride → N-(7-(cyclopropylamino)-3-formylpyrazolo[1,5-a]pyrimidin-5-yl)-2-fluorobenzamide

HRID 2037049Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2037049
[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.[F:17][C:18]1[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=1[C:20](Cl)=[O:21].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](=[O:21])[C:19]3[CH:23]=[CH:24][CH:25]=[CH:26][C:18]=3[F:17])[CH:7]=2)[CH2:11][CH2:10]1

Komponenten

5

Edukt 3

HCID 98082-Fluorobenzoyl chlorideHCID 81531DiisopropylethylamineHCID 583137635-Amino-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidine-3-carbaldehyde

Produkt 1

HCID 86654663N-(7-(cyclopropylamino)-3-formylpyrazolo[1,5-a]pyrimidin-5-yl)-2-fluorobenzamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To 5-amino-7-(cyclopropylamino) pyrazolo[1,5-a]pyrimidine-3-carbaldehyde (step b) (30 mg, 0.138 mmol) in 1.0 mL tetrahydrofuran, stirring under nitrogen, was added 2-fluoro benzoyl chloride (33 ul, 0.275 mmol) and DIPEA (28.8 ul). The reaction mixture was stirred at room temperature for one hour. The reaction was then partitioned between ethyl acetate and water, the organic layer was dried under sodium sulfate concentrated on high vacuum to yield N-(7-(cyclopropylamino)-3-formylpyrazolo[1,5-a]pyrimidin-5-yl)-2-fluorobenzamide. The crude product was further dissolved in 1.0 mL ethanol, added hydantoin (41.2 mg, 0.411 mmol) and pipperdine (40.0 ul). The reaction was heated to 80° C. for three hours. Cooled the reaction mixture and yellow precipitate was filtered, washed with ethanol to yield 10 mg (40% yield, two steps) (Z)-N-(7-(cyclopropylamino)-3-((2,5-dioxoimidazolidin-4-ylidene)methyl)pyrazolo[1,5-a]pyrimidin-5-yl)-2-fluorobenzamide. LCMS (M+1=422)

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-1603ba3ecc0d4a24b5969a518f705839
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08575177B2

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