1-Cyclopropyl-1-(5-methyl-1,2,4-oxadiazol-3-yl)ethan-1-amine → N-[1-cyclopropyl-1-(5-methyl-1,2,4-oxadiazol-3-yl)ethyl]-5-(3-fluorooxetan-3-yl)-4-[(2S)-1,1,1-trifluoropropan-2-yl]oxypyridine-2-carboxamide

HRID 1480240

Reaktionsgleichung

Reaktionsgleichung von HRID 1480240
[F:1][C:2]1([C:6]2[C:7]([O:15][C@@H:16]([CH3:21])[C:17]([F:20])([F:19])[F:18])=[CH:8][C:9]([C:12]([OH:14])=O)=[N:10][CH:11]=2)[CH2:5][O:4][CH2:3]1.[CH:22]1([C:25]([NH2:33])([C:27]2[N:31]=[C:30]([CH3:32])[O:29][N:28]=2)[CH3:26])[CH2:24][CH2:23]1>>[CH:22]1([C:25]([NH:33][C:12]([C:9]2[CH:8]=[C:7]([O:15][C@@H:16]([CH3:21])[C:17]([F:20])([F:19])[F:18])[C:6]([C:2]3([F:1])[CH2:5][O:4][CH2:3]3)=[CH:11][N:10]=2)=[O:14])([C:27]2[N:31]=[C:30]([CH3:32])[O:29][N:28]=2)[CH3:26])[CH2:24][CH2:23]1

Komponenten

3

Edukt 2

HCID 435592231-Cyclopropyl-1-(5-methyl-1,2,4-oxadiazol-3-yl)ethan-1-amineHCID 902149505-(3-fluorooxetan-3-yl)-4-[(1S)-2,2,2-trifluoro-1-methyl-ethoxy]pyridine-2-carboxylic acid

Produkt 1

HCID 90203576N-[1-cyclopropyl-1-(5-methyl-1,2,4-oxadiazol-3-yl)ethyl]-5-(3-fluorooxetan-3-yl)-4-[(2S)-1,1,1-trifluoropropan-2-yl]oxypyridine-2-carboxamide

Versuchsvorschrift

The title compound was synthesized in analogy to Example 112e, using 5-(3-fluorooxetan-3-yl)-4-[(1S)-2,2,2-trifluoro-1-methyl-ethoxy]pyridine-2-carboxylic acid (example 142b) and 1-Cyclopropyl-1-(5-methyl-[1,2,4]oxadiazol-3-yl)-ethylamine (CAN 1155536-64-3) as starting materials and the racemate was isolated (72 mg, 40%). The racemate was separated into its epimers by preparative chiral HPLC (Chiralpak AD, ethanol/heptane) and the title compound was the second epimer collected and isolated as colorless oil; MS (ESI, m/z): 459.5 (M+H+).

Aufarbeitung

  1. customthe racemate was isolated (72 mg, 40%)
  2. customThe racemate was separated into its epimers by preparative chiral HPLC (Chiralpak AD, ethanol/heptane)
  3. customcollected
  4. customisolated as colorless oil

Quellen und Nachweise

ORD-Eintrag
ord-c9bc730c99994b9aafcf74dc06ca6a9e
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09409866B2

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