1,1,1-Trichloropropanone → N-((1R,2R)-1-{[3,6-dicyclopropyl-5-(2,4-dichlorophenyl)pyrazin-2-yl]amino}-2,3-dihydro-1H-inden-2-yl)acetamide

HRID 1612356

Reaktionsgleichung

Reaktionsgleichung von HRID 1612356
[CH:1]1([C:4]2[C:5]([NH:21][C@@H:22]3[C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[CH2:24][C@H:23]3[NH2:31])=[N:6][C:7]([CH:18]3[CH2:20][CH2:19]3)=[C:8]([C:10]3[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=3[Cl:17])[N:9]=2)[CH2:3][CH2:2]1.Cl[C:33](Cl)(Cl)[C:34](=[O:36])C>C(Cl)(Cl)Cl>[CH:1]1([C:4]2[C:5]([NH:21][C@@H:22]3[C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[CH2:24][C@H:23]3[NH:31][C:34](=[O:36])[CH3:33])=[N:6][C:7]([CH:18]3[CH2:19][CH2:20]3)=[C:8]([C:10]3[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=3[Cl:17])[N:9]=2)[CH2:2][CH2:3]1

Komponenten

4

Edukt 2

HCID 135141,1,1-Trichloropropanone2×HCID 58583281(1R,2R)-N1-[3,6-dicyclopropyl-5-(2,4-dichlorophenyl)pyrazin-2-yl]-2,3-dihydro-1H-indene-1,2-diamine

Produkt 1

HCID 58583291N-((1R,2R)-1-{[3,6-dicyclopropyl-5-(2,4-dichlorophenyl)pyrazin-2-yl]amino}-2,3-dihydro-1H-inden-2-yl)acetamideAusbeute 101,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of (1R,2R)-N1-[3,6-dicyclopropyl-5-(2,4-dichlorophenyl)pyrazin-2-yl]-2,3-dihydro-1H-indene-1,2-diamine (0.10 g, 0.22 mmol) in CHCl3 (1 mL) at 0° C. under N2 was added trichloroacetone (30 μL, 0.26 mmol). The mixture was allowed to slowly warn to rt for 1.5 hr. The reaction was then heated at 60° C. for 1.5 h. Cool to rt, add additional trichloroacetone (10 μL) and continue heating at 60° C. for 2 hr. The reaction was concentrated and purified by biotage MPLC (90 g column, 80% ethyl acetate/hexanes) to afford 0.11 g (55%) of N-((1R,2R)-1-{[3,6-dicyclopropyl-5-(2,4-dichlorophenyl)pyrazin-2-yl]amino}-2,3-dihydro-1H-inden-2-yl)acetamide as a solid: 1H NMR (CDCl3) δ 0.84-1.01, 1.61-1.81, 2.04, 2.80-2.86, 3.58-3.64, 4.07-4.13, 4.46, 5.56, 6.56, 7.28-7.51; MS (ESI+) for C27H26Cl2N4O m/z 493 (M+H)+.

Aufarbeitung

  1. temperatureCool to rt
  2. temperaturecontinue heating at 60° C. for 2 hr
  3. concentrationThe reaction was concentrated
  4. custompurified by biotage MPLC (90 g column, 80% ethyl acetate/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-2938c05cc08f40c3ba3f978cffde5255
Quelldatensatz
uspto-grants-2006_01
Patentnummer
US06992087B2

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