1-Cyclopropyl-1-(5-methyl-1,2,4-oxadiazol-3-yl)ethan-1-amine → 5-Cyclopropyl-4-((S)-2,2,2-trifluoro-1-methyl-ethoxy)-pyridine-2-carboxylic acid [1-cyclopropyl-1-(5-methyl-[1,2,4]oxadiazol-3-yl)-ethyl]-amide

HRID 1480130

Reaktionsgleichung

Reaktionsgleichung von HRID 1480130
[CH:1]1([C:4]2[C:5]([O:13][C@@H:14]([CH3:19])[C:15]([F:18])([F:17])[F:16])=[CH:6][C:7]([C:10]([OH:12])=O)=[N:8][CH:9]=2)[CH2:3][CH2:2]1.[CH:20]1([C:23]([NH2:31])([C:25]2[N:29]=[C:28]([CH3:30])[O:27][N:26]=2)[CH3:24])[CH2:22][CH2:21]1>>[CH:20]1([C:23]([NH:31][C:10]([C:7]2[CH:6]=[C:5]([O:13][C@@H:14]([CH3:19])[C:15]([F:18])([F:17])[F:16])[C:4]([CH:1]3[CH2:2][CH2:3]3)=[CH:9][N:8]=2)=[O:12])([C:25]2[N:29]=[C:28]([CH3:30])[O:27][N:26]=2)[CH3:24])[CH2:22][CH2:21]1

Komponenten

3

Edukt 2

HCID 435592231-Cyclopropyl-1-(5-methyl-1,2,4-oxadiazol-3-yl)ethan-1-amineHCID 902045735-Cyclopropyl-4-((S)-2,2,2-trifluoro-1-methyl-ethoxy)-pyridine-2-carboxylic acid

Produkt 1

HCID 747638225-Cyclopropyl-4-((S)-2,2,2-trifluoro-1-methyl-ethoxy)-pyridine-2-carboxylic acid [1-cyclopropyl-1-(5-methyl-[1,2,4]oxadiazol-3-yl)-ethyl]-amide

Versuchsvorschrift

The mixture of epimers was synthesized in analogy to Example 63b, using 5-Cyclopropyl-4-((S)-2,2,2-trifluoro-1-methyl-ethoxy)-pyridine-2-carboxylic acid (Example 68a) and 1-Cyclopropyl-1-(5-methyl-[1,2,4]oxadiazol-3-yl)-ethylamine (CAN 1155536-64-3) as starting materials and isolated (135 mg, 58%) as a light yellow oil. The mixture of epimers was separated into its epimers by preparative chiral HPLC (Chiralpak AD, ethanol/heptane) and the title compound was the first epimer collected and isolated as colorless oil; MS (ESI, m/z): 425.5 (M+H+).

Aufarbeitung

  1. additionThe mixture of epimers
  2. customwas synthesized in analogy to Example 63b
  3. customisolated (135 mg, 58%) as a light yellow oil
  4. additionThe mixture of epimers
  5. customwas separated into its epimers by preparative chiral HPLC (Chiralpak AD, ethanol/heptane)
  6. customcollected
  7. customisolated as colorless oil

Quellen und Nachweise

ORD-Eintrag
ord-9f5cf8f5488242eda0e56fe2de91689e
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09409866B2

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