Hydrochloric Acid → rac-2-[(1R,2R,4S)-bicyclo[2.2.1]hept-2-ylamino]-4-(trifluoromethyl)pyrimidine-5-carboxylic acid

HRID 38765Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 38765
[C@H:1]12[CH2:7][C@H:4]([CH2:5][CH2:6]1)[CH2:3][C@H:2]2[NH:8][C:9]1[N:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[C:12]([C:19]([O:21]C)=[O:20])=[CH:11][N:10]=1.CO.[OH-].[Na+].Cl>O1CCCC1>[C@H:1]12[CH2:7][C@H:4]([CH2:5][CH2:6]1)[CH2:3][C@H:2]2[NH:8][C:9]1[N:14]=[C:13]([C:15]([F:16])([F:17])[F:18])[C:12]([C:19]([OH:21])=[O:20])=[CH:11][N:10]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 66720228methyl rac-2-[(1R,2R,4S)-bicyclo[2.2.1]hept-2-ylamino]-4-(trifluoromethyl)pyrimidine-5-carboxylate

Produkt 1

HCID 66720245rac-2-[(1R,2R,4S)-bicyclo[2.2.1]hept-2-ylamino]-4-(trifluoromethyl)pyrimidine-5-carboxylic acidAusbeute 98,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a mixture of methyl rac-2-[(1R,2R,4S)-bicyclo[2.2.1]hept-2-ylamino]-4-(trifluoromethyl)pyrimidine-5-carboxylate (5.2 g), methanol (25 mL), and tetrahydrofuran (25 mL) was added a 1 M aqueous sodium hydroxide solution (33 mL) at room temperature, followed by stirring at 60° C. for 2 hours. To the reaction mixture was added 1 M hydrochloric acid, followed by stirring at room temperature for 30 minutes, and then the precipitate was collected by filtration and washed with water to obtain rac-2-[(1R,2R,4S)-bicyclo[2.2.1]hept-2-ylamino]-4-(trifluoromethyl)pyrimidine-5-carboxylic acid (4.9 g) as a white powder.

Aufarbeitung

  1. stirringby stirring at room temperature for 30 minutes
  2. filtrationthe precipitate was collected by filtration
  3. washwashed with water

Quellen und Nachweise

ORD-Eintrag
ord-d1e4dfcea73745eba96951d7852036f1
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524727B2

Notizen zur Reaktion

Wird geladen…