Propionyl chloride → (rac)-N-(4-(3-Fluoro-4-(trifluoromethyl)phenyl)-6,7-dihydro-5H-cyclopenta[c]pyridin-7-yl)propionamide

HRID 714098Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 714098
[F:1][C:2]1[CH:3]=[C:4]([C:12]2[C:20]3[CH2:19][CH2:18][CH:17]([NH2:21])[C:16]=3[CH:15]=[N:14][CH:13]=2)[CH:5]=[CH:6][C:7]=1[C:8]([F:11])([F:10])[F:9].C(N(CC)C(C)C)(C)C.[C:31](Cl)(=[O:34])[CH2:32][CH3:33]>CN(C=O)C>[F:1][C:2]1[CH:3]=[C:4]([C:12]2[C:20]3[CH2:19][CH2:18][CH:17]([NH:21][C:31](=[O:34])[CH2:32][CH3:33])[C:16]=3[CH:15]=[N:14][CH:13]=2)[CH:5]=[CH:6][C:7]=1[C:8]([F:9])([F:11])[F:10]

Komponenten

5

Edukt 3

HCID 62324Propionyl chlorideHCID 81531DiisopropylethylamineHCID 71811529(rac)-4-(3-Fluoro-4-trifluoromethyl-phenyl)-6,7-dihydro-5H-[2]pyrindin-7-ylamine

Produkt 1

HCID 71811528(rac)-N-(4-(3-Fluoro-4-(trifluoromethyl)phenyl)-6,7-dihydro-5H-cyclopenta[c]pyridin-7-yl)propionamideAusbeute 8,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of (rac)-4-(3-fluoro-4-trifluoromethyl-phenyl)-6,7-dihydro-5H-[2]pyrindin-7-ylamine (example 89) (40 mg, 0.14 mmol) and N,N-diisopropylethylamine (0.071 mL, 0.41 mmol) in DMF (0.5 mL) was treated with propionyl chloride (0.018 mL, 0.20 mmol) and the reaction mixture stirred at room temperature overnight. Purification by preparative HPLC on reversed phase eluting with a gradient of acetonitrile/water provided 4.0 mg (7%) of the title compound as a light brown oil. MS: 353.5 (M+H)+.

Aufarbeitung

  1. customPurification by preparative HPLC on reversed phase
  2. washeluting with a gradient of acetonitrile/water

Quellen und Nachweise

ORD-Eintrag
ord-9edfb4aa6e314287a2610a1c03de54f1
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09187429B2

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