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

HRID 714810
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 714810
[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]([NH:28][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]([NH:28][CH3:29])=[O:27])[CH:24]=3)[N:7]=2)[C:9]1=[O:18])#[N:14]
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Komponenten

5

Edukt 3

HCID 176Acetic AcidHCID 280651732-(4-amino-1H-pyrazol-1-yl)-N-methylacetamideHCID 117840068(3S)-1-(2-chloropyrimidin-4-yl)-3-isopropyl-2-oxopyrrolidine-3-carbonitrile

Produkt 1

HCID 1178408692-(4-((4-((3S)-3-cyano-3-isopropyl-2-oxopyrrolidin-1-yl) pyrimidin-2-yl)amino)-1H-pyrazol-1-yl)-N-methylacetamide hydrochlorideAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702
Ethanol
Lösungsmittel

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-methylacetamide (38 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 (83 mg) in ethanol (3 mL) was added 1M hydrochloric acid (220 μL), and the solvent was evaporated under reduced pressure. The residue was recrystallized (diisopropyl ether/ethanol) to give the title compound (87 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 (83 mg) in ethanol (3 mL) was added 1M hydrochloric acid (220 μL)
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was recrystallized (diisopropyl ether/ethanol)

Quellen und Nachweise

ORD-Eintrag
ord-be445a605af5482699947619dfd495a2
Quelldatensatz
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09187453B2

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