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

HRID 714794
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 714794
[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:29]=[CH:28][C:23]([C:24]([NH:26][CH3:27])=[O:25])=[CH:22][CH:21]=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]=[CH:22][C:23]([C:24]([NH:26][CH3:27])=[O:25])=[CH:28][CH:29]=3)[N:7]=2)[C:9]1=[O:18])#[N:14]
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Komponenten

5

Edukt 3

HCID 176Acetic AcidHCID 2355164-Amino-N-methylbenzamideHCID 117840068(3S)-1-(2-chloropyrimidin-4-yl)-3-isopropyl-2-oxopyrrolidine-3-carbonitrile

Produkt 1

HCID 1178406794-((4-((3S)-3-cyano-3-isopropyl-2-oxopyrrolidin-1-yl) pyrimidin-2-yl)amino)-N-methylbenzamide hydrochlorideAusbeute 75,4 %

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, 4-amino-N-methylbenzamide (37 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, hexane/ethyl acetate). To a solution of the residue (87 mg) in ethanol (3 mL) was added 1M hydrochloric acid (230 μL), and the solvent was evaporated under reduced pressure. The residue was recrystallized (diisopropyl ether/ethanol) to give the title compound (65 mg).

Aufarbeitung

  1. customthe solvent was evaporated under reduced pressure
  2. customThe obtained residue was purified by silica gel column chromatography (NH, hexane/ethyl acetate)
  3. additionTo a solution of the residue (87 mg) in ethanol (3 mL) was added 1M hydrochloric acid (230 μL)
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was recrystallized (diisopropyl ether/ethanol)

Quellen und Nachweise

ORD-Eintrag
ord-001b6de79426471f9347ff939e9a0b5c
Quelldatensatz
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09187453B2

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