Methyl acetoacetate → HCID 73331551, Verbindung

HRID 63686

Reaktionsgleichung

Reaktionsgleichung von HRID 63686
[Cl:1][C:2]1[C:9]([F:10])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.[C:11]([O:17][CH2:18][CH3:19])(=[O:16])[CH2:12][C:13]([CH3:15])=O.[CH3:20][N:21]1[CH:25]=[CH:24][N:23]=[C:22]1[C:26]#[N:27].[NH:28]1[CH2:33][CH2:32][O:31][CH2:30][C@H:29]1[C:34]([OH:36])=[O:35].C(OC)(=O)CC(C)=O.S1C=C[N:47]=C1C#N.FC1(F)CN[C@H](C(O)=O)C1>>[Cl:1][C:2]1[C:9]([F:10])=[CH:8][CH:7]=[CH:6][C:3]=1[C@@H:4]1[N:47]=[C:26]([C:22]2[N:21]([CH3:20])[CH:25]=[CH:24][N:23]=2)[NH:27][C:13]([CH2:15][N:28]2[CH2:33][CH2:32][O:31][CH2:30][C@H:29]2[C:34]([OH:36])=[O:35])=[C:12]1[C:11]([O:17][CH2:18][CH3:19])=[O:16]

Komponenten

8

Edukt 7

HCID 7757Methyl acetoacetateHCID 8868Ethyl AcetoacetateHCID 1501894(S)-morpholine-3-carboxylic acidHCID 109534431-Methyl-1H-imidazole-2-carbonitrileHCID 149449052-Chloro-3-fluorobenzaldehydeHCID 151114801,3-Thiazole-2-carbonitrileHCID 152161024,4-Difluoroproline

Produkt 1

HCID 73331551HCID 73331551, Verbindung

Versuchsvorschrift

The title compound was prepared in analogy to Example 2 with Procedure B shown in Scheme 5 by using 2-chloro-3-fluoro-benzaldehyde, ethyl acetoacetate, 1-methyl-1H-imidazole-2-carbonitrile and (S)-morpholine-3-carboxylic acid instead of 2-chloro-4-fluoro-benzaldehyde, methyl acetoacetate, thiazole-2-carbonitrile and (S)-4,4-difluoro-pyrrolidine-2-carboxylic acid. The stereochemistry of Example 97 was determined by comparing its 1H NMR data and HPLC retention time with Example 2.

Quellen und Nachweise

ORD-Eintrag
ord-2099ff62d97b47c7bf9b35d3db29fc75
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09447086B2

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