Diisopropylethylamine → HCID 56832632, Verbindung

HRID 920975Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 920975
[F:1][C:2]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15](=[O:22])[NH:14][N:13]=2)=[CH:7][C:3]=1[C:4](O)=[O:5].F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.Cl.[N:48]1[N:49]=[CH:50][N:51]2[CH2:56][CH2:55][NH:54][CH2:53][C:52]=12.C(N(CC)C(C)C)(C)C>CN(C)C=O>[N:48]1[N:49]=[CH:50][N:51]2[CH2:56][CH2:55][N:54]([C:4]([C:3]3[CH:7]=[C:8]([CH2:11][C:12]4[C:21]5[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=5)[C:15](=[O:22])[NH:14][N:13]=4)[CH:9]=[CH:10][C:2]=3[F:1])=[O:5])[CH2:53][C:52]=12

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 17998717HCID 17998717, VerbindungHCID 248117402-Fluoro-5-[(4-oxo-3,4-dihydrophthalazin-1-yl)methyl]benzoic acid

Produkt 1

HCID 56832632HCID 56832632, VerbindungAusbeute 21,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

2-Fluoro-5-[(4-oxo-3H-phthalazin-1-yl)methyl]benzoic acid 1a (170 mg, 0.57 mmol) was dissolved in 10 mL of N,N-dimethylformamide, followed by addition of O-(1-benzotriazolyl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (323 mg, 0.85 mmol), 5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride 17a (100 mg, 0.63 mmol, prepared according to a known method “Journal of Medicinal Chemistry, 2005, 48(1), 141-151”) and N,N-diisopropylethylamine (302 mg, 1.70 mmol). After stirring for 12 hours, the reaction mixture was concentrated under reduced pressure and the resulting residue was purified by thin layer chromatography with elution system A to obtain 4-[[3-(6,8-dihydro-5H-[1,2,4]triazolo[4,3-a]pyrazine-7-carbonyl)-4-fluoro-phenyl]methyl]-2H-phthalazin-1-one 17 (50 mg, yield 21.7%) as a light yellow solid.

Aufarbeitung

  1. customprepared
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. customthe resulting residue was purified by thin layer chromatography with elution system

Quellen und Nachweise

ORD-Eintrag
ord-9a012be727134b95a9dde794a7c3fd24
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09273052B2

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