Hydrochloric Acid → N2-(4,4-dimethyl-4H-benzo[b]tetrazolo[1,5-d][1,4]oxazin-8-yl)-5-fluoro-N4-(octahydro-5,5-dimethylindolizin-7-yl)pyrimidine-2,4-diamine

HRID 633356Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 633356
Cl[C:2]1[N:7]=[C:6]([NH:8][CH:9]2[CH2:17][CH:16]3[N:12]([CH2:13][CH2:14][CH2:15]3)[C:11]([CH3:19])([CH3:18])[CH2:10]2)[C:5]([F:20])=[CH:4][N:3]=1.[CH3:21][C:22]1([CH3:37])[O:27][C:26]2[C:28](F)=[CH:29][C:30]([NH2:32])=[CH:31][C:25]=2[N:24]2[N:34]=[N:35][N:36]=[C:23]12.Cl>CC(O)C.O1CCOCC1>[CH3:21][C:22]1([CH3:37])[O:27][C:26]2[CH:28]=[CH:29][C:30]([NH:32][C:2]3[N:7]=[C:6]([NH:8][CH:9]4[CH2:17][CH:16]5[N:12]([CH2:13][CH2:14][CH2:15]5)[C:11]([CH3:19])([CH3:18])[CH2:10]4)[C:5]([F:20])=[CH:4][N:3]=3)=[CH:31][C:25]=2[N:24]2[N:34]=[N:35][N:36]=[C:23]12

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 86704443N-(2-chloro-5-fluoropyrimidin-4-yl)-octahydro-5,5-dimethylindolizin-7-amineHCID 867044684,4-dimethyl-6-fluoro-4H-benzo[b]tetrazolo[1,5-d][1,4]oxazin-8-amine

Produkt 1

HCID 86704467N2-(4,4-dimethyl-4H-benzo[b]tetrazolo[1,5-d][1,4]oxazin-8-yl)-5-fluoro-N4-(octahydro-5,5-dimethylindolizin-7-yl)pyrimidine-2,4-diamineAusbeute 83,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3776IsopropanolLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A solution of (R/S,S/R)—N-(2-chloro-5-fluoropyrimidin-4-yl)-octahydro-5,5-dimethylindolizin-7-amine (D1) (0.1 g, 0.3 mmol, single diastereomer) in 3 ml of iPrOH, 4,4-dimethyl-6-fluoro-4H-benzo[b]tetrazolo[1,5-d][1,4]oxazin-8-amine (0.093 g, 0.4 mmol) and 4N HCl in dioxane (0.1 ml) were added. The reaction mixture was heated to 100° C. in a sealed vial for 12 hours. LCMS analysis of the crude reaction mixture indicated the completion of the reaction. The crude product was purified by column chromatography to give 0.12 g (Yield=72%) of the product as a mixture of two enantiomers.

Aufarbeitung

  1. customLCMS analysis of the crude reaction mixture
  2. customthe completion of the reaction
  3. customThe crude product was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-e869dd3813f147fda95b26e62f82ffc5
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09321763B2

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