Ethanolamine → 5-((2S,4R)-1-acetyl-4-((5-cyanopyrazin-2-yl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)-N-(2-hydroxyethyl)picolinamide

HRID 882291Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 882291
[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]3[CH:15]=[CH:16][C:17]([C:20]([OH:22])=O)=[N:18][CH:19]=3)=[CH:11][CH:12]=2)[C@H:7]([NH:23][C:24]2[CH:29]=[N:28][C:27]([C:30]#[N:31])=[CH:26][N:25]=2)[CH2:6][C@@H:5]1[CH3:32])(=[O:3])[CH3:2].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[NH2:66][CH2:67][CH2:68][OH:69]>CN(C=O)C>[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]3[CH:15]=[CH:16][C:17]([C:20]([NH:66][CH2:67][CH2:68][OH:69])=[O:22])=[N:18][CH:19]=3)=[CH:11][CH:12]=2)[C@H:7]([NH:23][C:24]2[CH:29]=[N:28][C:27]([C:30]#[N:31])=[CH:26][N:25]=2)[CH2:6][C@@H:5]1[CH3:32])(=[O:3])[CH3:2]

Komponenten

6

Edukt 4

HCID 700EthanolamineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 867094225-((2S,4R)-1-acetyl-4-((5-cyanopyrazin-2-yl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)picolinic acid

Produkt 1

HCID 714682585-((2S,4R)-1-acetyl-4-((5-cyanopyrazin-2-yl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)-N-(2-hydroxyethyl)picolinamideAusbeute 38 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

5-((2S,4R)-1-acetyl-4-((5-cyanopyrazin-2-yl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)picolinic acid (for a preparation see Intermediate 53) (100 mg, 0.233 mmol), HATU (177 mg, 0.467 mmol) and DIPEA (0.122 ml, 0.700 mmol) were combined in DMF (3 mL) and stirred at room temperature for 10 mins. 2-aminoethanol (0.029 ml, 0.350 mmol) was added and the reaction mixture stirred for 1.5 h. The mixture was concentrated in vacuo and purified by MDAP (formate) to give 5-((2S,4R)-1-acetyl-4-((5-cyanopyrazin-2-yl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)-N-(2-hydroxyethyl)picolinamide (42 mg, 0.089 mmol, 38% yield). LCMS: (Formate, 2 min), Rt=0.73 mins, MH+=472

Aufarbeitung

  1. stirringthe reaction mixture stirred for 1.5 h
  2. concentrationThe mixture was concentrated in vacuo
  3. custompurified by MDAP (formate)

Quellen und Nachweise

ORD-Eintrag
ord-aebe6c458d3745b2b4c199d98bc7146a
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08993554B2

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