3-Aminopyridine → HCID 57625993, Verbindung

HRID 546574

Reaktionsgleichung

Reaktionsgleichung von HRID 546574
Cl[C:2]1[CH:7]=[C:6]([CH2:8][N:9]2[C:13]([CH3:15])([CH3:14])[C:12](=[O:16])[N:11]([C:17]3[CH:18]=[CH:19][C:20]([S:50][C:51]([F:54])([F:53])[F:52])=[C:21]([NH:23][C:24](=[O:49])[C@H:25]([NH:32]C(=O)CC4C5C=CC=CC=5C5C4=CC=CC=5)[C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[CH:22]=3)[C:10]2=[O:55])[CH:5]=[CH:4][N:3]=1.[NH2:56][C:57]1[CH:58]=[N:59][CH:60]=[CH:61][CH:62]=1.CC1(C)C2C=CC(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=2OC2C1=CC=C(P(C1C=CC=CC=1)C1C=CC=CC=1)C=2.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[NH2:32][C@H:25]([C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)[C:24]([NH:23][C:21]1[CH:22]=[C:17]([N:11]2[C:12](=[O:16])[C:13]([CH3:14])([CH3:15])[N:9]([CH2:8][C:6]3[CH:5]=[CH:4][N:3]=[C:2]([NH:56][C:57]4[CH:58]=[N:59][CH:60]=[CH:61][CH:62]=4)[CH:7]=3)[C:10]2=[O:55])[CH:18]=[CH:19][C:20]=1[S:50][C:51]([F:52])([F:54])[F:53])=[O:49]

Komponenten

7

Edukt 4

HCID 100093-AminopyridineHCID 10796Cesium carbonateHCID 57625996HCID 57625996, VerbindungHCID 86628973(9,9-dimethyl-9H-xanthene-3,6-diyl)bis(diphenylphosphine)

Produkt 1

HCID 57625993HCID 57625993, VerbindungAusbeute 18,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

To a solution of 33 mg of (2R)—N-(5-{3-[(2-chloropyridin-4-yl)methyl]-4,4-dimethyl-2,5-dioxoimidazolidin-1-yl}-2-[(trifluoromethyl)thio]phenyl)-2-[(9H-fluoren-9-ylacetyl)-amino]-2-phenylacetamide obtained in stage e) below in 1 mL of dioxane are successively added, under argon, 14 mg of 3-aminopyridine, 3 mg of (9,9-dimethyl-9H-xanthene-3,6-diyl)bis(diphenylphosphine) (Xantphos), 1.1 mg of palladium acetate and 61 mg of caesium carbonate. The reaction mixture is heated at 110° C. for 3 h, filtered and washed with twice 10 mL of dioxane, and the filtrate is then concentrated under reduced pressure. The residue is purified by HPLC (gradient: water/acetonitrile containing 0.1% formic acid) to give 5 mg of (2R)-2-amino-N-{5-(4,4-dimethyl-2,5-dioxo-3-{[2-(pyridin-3-ylamino)pyridin-4-yl]methyl}imidazolidin-1-yl)-2-[(trifluoromethyl)thio]phenyl}-2-phenylacetamide, the characteristics of which are as follows:

Aufarbeitung

  1. filtrationfiltered
  2. washwashed with twice 10 mL of dioxane
  3. concentrationthe filtrate is then concentrated under reduced pressure
  4. customThe residue is purified by HPLC (gradient: water/acetonitrile containing 0.1% formic acid)

Quellen und Nachweise

ORD-Eintrag
ord-33baa980e60e4924a399c02ff955abce
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07935819B2

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