Methanol → 5-Cyclopropyl-6-cyclopropylmethoxy-pyridine-2-carboxylic acid [(+)-2-cyclopropyl-1-methyl-1-(5-methyl-[1,2,4]oxadiazol-3-yl)-ethyl]-amide

HRID 632437Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 632437
[CH:1]1([C:4]2[CH:5]=[CH:6][C:7]([C:15]([OH:17])=O)=[N:8][C:9]=2[O:10][CH2:11][CH:12]2[CH2:14][CH2:13]2)[CH2:3][CH2:2]1.[CH:18]1([CH2:21][C:22]([NH2:30])([CH3:29])[C:23]2[N:27]=[C:26]([CH3:28])[O:25][N:24]=2)[CH2:20][CH2:19]1.CO>CCCCCCC>[CH:18]1([CH2:21][C:22]([NH:30][C:15]([C:7]2[CH:6]=[CH:5][C:4]([CH:1]3[CH2:2][CH2:3]3)=[C:9]([O:10][CH2:11][CH:12]3[CH2:13][CH2:14]3)[N:8]=2)=[O:17])([CH3:29])[C:23]2[N:27]=[C:26]([CH3:28])[O:25][N:24]=2)[CH2:20][CH2:19]1

Komponenten

5

Edukt 3

HCID 887MethanolHCID 710873465-Cyclopropyl-6-cyclopropylmethoxy-pyridine-2-carboxylic acidHCID 710877912-Cyclopropyl-1-methyl-1-(5-methyl-[1,2,4]oxadiazol-3-yl)-ethylamine

Produkt 1

HCID 780101935-Cyclopropyl-6-cyclopropylmethoxy-pyridine-2-carboxylic acid [(+)-2-cyclopropyl-1-methyl-1-(5-methyl-[1,2,4]oxadiazol-3-yl)-ethyl]-amide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8900HeptaneLösungsmittel

Versuchsvorschrift

The title compound was synthesized in analogy to Example 1, using 5-cyclopropyl-6-cyclopropylmethyloxy-pyridine-2-carboxylic acid (Example 42a) and 2-cyclopropyl-1-methyl-1-(5-methyl-[1,2,4]oxadiazol-3-yl)-ethylamine (Example 357e) as starting materials. The product was isolated by chiral chromatography on Reprosil Chiral NR using heptane/10% 2-propanol as eluent. The (−)-enantiomer was isolated. LC-MS (UV peak area/ESI) 100%, 397.2244 (M+H)+, αD20 (MeOH)=−22.3°.

Aufarbeitung

  1. customThe product was isolated by chiral chromatography on Reprosil Chiral NR
  2. customThe (−)-enantiomer was isolated

Quellen und Nachweise

ORD-Eintrag
ord-49dfd939b866464dbd2a39175da984a0
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09321727B2

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