Hydrochloric Acid → 3-(Aminomethyl)-6-methyl-4-(trifluoromethyl)-1,2-dihydropyridin-2-one hydrochloride HCl salt

HRID 2208657Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2208657
[CH3:1][C:2]1[NH:7][C:6](=[O:8])[C:5]([C:9]#[N:10])=[C:4]([C:11]([F:14])([F:13])[F:12])[CH:3]=1.N#N.[ClH:17]>CO.[OH-].[OH-].[Pd+2]>[ClH:17].[ClH:17].[NH2:10][CH2:9][C:5]1[C:6](=[O:8])[NH:7][C:2]([CH3:1])=[CH:3][C:4]=1[C:11]([F:12])([F:13])[F:14]

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 947Nitrogen2×HCID 2474406-Methyl-2-oxo-4-(trifluoromethyl)-1,2-dihydropyridine-3-carbonitrile

Produkt 1

HCID 901508353-(Aminomethyl)-6-methyl-4-(trifluoromethyl)-1,2-dihydropyridin-2-one hydrochloride HCl saltAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9942167Palladium hydroxideKatalysatorHCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
23 °C

Versuchsvorschrift

To a solution of 6-methyl-2-oxo-4-(trifluoromethyl)-1,2-dihydropyridine-3-carbonitrile (400 mg, 1.98 mmol) in MeOH (19.8 ml) and HCl (436 ul, 12M) was added 10% Pd(OH)2 (361 mg, 0.257 mmol) under N2 atmosphere. The N2 gas was displaced by H2 gas and the mixture was stirred for 18 h at 23° C. under hydrogen. The H2 gas was displaced by N2 gas. The mixture was filtered through Celite, washed with MeOH and concentrated. The residue was triturated with MeOH-Et2O, collected with Buchner funnel, and dried in vacuo to give the titled compound (433 mg, 100%). 1H NMR (400 MHz, DMSO-d6): δ ppm 2.31 (s, 3H), 3.88 (s, 2H), 6.43 (s, 1H).

Aufarbeitung

  1. filtrationThe mixture was filtered through Celite
  2. washwashed with MeOH
  3. concentrationconcentrated
  4. customThe residue was triturated with MeOH-Et2O
  5. customcollected with Buchner funnel
  6. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-c8703142aed845d78710af68f2150acb
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09376422B2

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