Acetic Acid → 2-(4-((4-((3S)-3-cyano-3-isopropyl-2-oxopyrrolidin-1-yl)pyrimidin-2-yl)amino)-1H-pyrazol-1-yl)-N,N-dimethylacetamide hydrochloride

HRID 714811Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 714811
[Cl:1][C:2]1[N:7]=[C:6]([N:8]2[CH2:12][CH2:11][C@:10]([CH:15]([CH3:17])[CH3:16])([C:13]#[N:14])[C:9]2=[O:18])[CH:5]=[CH:4][N:3]=1.[NH2:19][C:20]1[CH:21]=[N:22][N:23]([CH2:25][C:26]([N:28]([CH3:30])[CH3:29])=[O:27])[CH:24]=1.C(O)(=O)C>C(O)C>[ClH:1].[C:13]([C@@:10]1([CH:15]([CH3:17])[CH3:16])[CH2:11][CH2:12][N:8]([C:6]2[CH:5]=[CH:4][N:3]=[C:2]([NH:19][C:20]3[CH:21]=[N:22][N:23]([CH2:25][C:26]([N:28]([CH3:30])[CH3:29])=[O:27])[CH:24]=3)[N:7]=2)[C:9]1=[O:18])#[N:14]

Komponenten

5

Edukt 3

HCID 176Acetic AcidHCID 282806662-(4-amino-1H-pyrazol-1-yl)-N,N-dimethylacetamideHCID 117840068(3S)-1-(2-chloropyrimidin-4-yl)-3-isopropyl-2-oxopyrrolidine-3-carbonitrile

Produkt 1

HCID 1178407032-(4-((4-((3S)-3-cyano-3-isopropyl-2-oxopyrrolidin-1-yl)pyrimidin-2-yl)amino)-1H-pyrazol-1-yl)-N,N-dimethylacetamide hydrochlorideAusbeute 100,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of (3S)-1-(2-chloropyrimidin-4-yl)-3-isopropyl-2-oxopyrrolidine-3-carbonitrile (55 mg) obtained in Step A of Example 9, 2-(4-amino-1H-pyrazol-1-yl)-N,N-dimethylacetamide (42 mg) and acetic acid (13 μL) in ethanol (2 mL) was stirred in a microwave reactor at 150° C. for 1 hr, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (NH, ethyl acetate/methanol). To a solution of the residue (80 mg) in ethanol (3 mL) was added 1M hydrochloric acid (200 μL), and the solvent was evaporated under reduced pressure. The residue was recrystallized (diisopropyl ether/ethanol) to give the title compound (90 mg).

Aufarbeitung

  1. customthe solvent was evaporated under reduced pressure
  2. customThe obtained residue was purified by silica gel column chromatography (NH, ethyl acetate/methanol)
  3. additionTo a solution of the residue (80 mg) in ethanol (3 mL) was added 1M hydrochloric acid (200 μL)
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was recrystallized (diisopropyl ether/ethanol)

Quellen und Nachweise

ORD-Eintrag
ord-7a1659359c0e443998816e5d6557b7f8
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09187453B2

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