Dimethylamine → (S)-5-chloro-6-(4-(3-(2-fluoro-4-(methylsulfonyl)phenylamino)-2-oxopyrrolidin-1-yl)piperidin-1-yl)-N,N-dimethylnicotinamide

HRID 408014Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 408014
[Cl:1][C:2]1[C:3]([N:11]2[CH2:16][CH2:15][CH:14]([N:17]3[CH2:21][CH2:20][C@H:19]([NH:22][C:23]4[CH:28]=[CH:27][C:26]([S:29]([CH3:32])(=[O:31])=[O:30])=[CH:25][C:24]=4[F:33])[C:18]3=[O:34])[CH2:13][CH2:12]2)=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7](Cl)=[O:8].[CH3:35][NH:36][CH3:37]>CN(C=O)C.C(#N)C.C1COCC1.CCOC(C)=O>[Cl:1][C:2]1[C:3]([N:11]2[CH2:16][CH2:15][CH:14]([N:17]3[CH2:21][CH2:20][C@H:19]([NH:22][C:23]4[CH:28]=[CH:27][C:26]([S:29]([CH3:32])(=[O:31])=[O:30])=[CH:25][C:24]=4[F:33])[C:18]3=[O:34])[CH2:13][CH2:12]2)=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7]([N:36]([CH3:37])[CH3:35])=[O:8]

Komponenten

5

Edukt 2

HCID 674DimethylamineHCID 86688120(S)-5-chloro-6-(4-(3-(2-fluoro-4-(methylsulfonyl)phenylamino)-2-oxopyrrolidin-1-yl)piperidin-1-yl)nicotinoyl chloride

Produkt 1

HCID 54670712(S)-5-chloro-6-(4-(3-(2-fluoro-4-(methylsulfonyl)phenylamino)-2-oxopyrrolidin-1-yl)piperidin-1-yl)-N,N-dimethylnicotinamideAusbeute 39,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8857Ethyl AcetateLösungsmittelHCID 86691292Dmf acn thfLösungsmittel

Versuchsvorschrift

To a solution of (S)-5-chloro-6-(4-(3-(2-fluoro-4-(methylsulfonyl)phenylamino)-2-oxopyrrolidin-1-yl)piperidin-1-yl)nicotinoyl chloride (0.15 g, 0.28 mmol) in 5 mL of DMF/ACN/THF (1:1:1) was added dimethylamine (2 M solution in THF, 1.4 mL, 2.8 mmol) and the reaction was stirred at ambient temperature for 4 hours. The reaction was diluted with EtOAc (100 mL) and the organic layer was washed with water (20 mL) and brine (20 mL), and the organic layer was dried over MgSO4, and concentrated under vacuum. The material was triturated with isopropanol (about 6 mL) to give (S)-5-chloro-6-(4-(3-(2-fluoro-4-(methylsulfonyl)phenylamino)-2-oxopyrrolidin-1-yl)piperidin-1-yl)-N,N-dimethylnicotinamide (0.059 g, 0.11 mmol, 38% yield). Mass spectrum (apci) m/z=538.0 (M+H).

Aufarbeitung

  1. washthe organic layer was washed with water (20 mL) and brine (20 mL)
  2. dry with materialthe organic layer was dried over MgSO4
  3. concentrationconcentrated under vacuum
  4. customThe material was triturated with isopropanol (about 6 mL)

Quellen und Nachweise

ORD-Eintrag
ord-4f4b49fd18794cc582b2f033d713457f
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08754226B2

Notizen zur Reaktion

Wird geladen…