Pyridine → Methyl [1-(3-{[(2S,3R)-2-(4-chlorophenyl)-4,4,4-trifluoro-3-methylbutanoyl]amino}-4-fluorophenyl)cyclopropyl]acetate

HRID 1476085Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1476085
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([C@@H:12]([CH3:17])[C:13]([F:16])([F:15])[F:14])[C:9]([OH:11])=O)=[CH:4][CH:3]=1.[NH2:18][C:19]1[CH:20]=[C:21]([C:26]2([CH2:29][C:30]([O:32][CH3:33])=[O:31])[CH2:28][CH2:27]2)[CH:22]=[CH:23][C:24]=1[F:25].F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.N1C=CC=CC=1>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C@H:8]([C@@H:12]([CH3:17])[C:13]([F:16])([F:15])[F:14])[C:9]([NH:18][C:19]2[CH:20]=[C:21]([C:26]3([CH2:29][C:30]([O:32][CH3:33])=[O:31])[CH2:27][CH2:28]3)[CH:22]=[CH:23][C:24]=2[F:25])=[O:11])=[CH:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 1049PyridineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58288274Methyl [1-(3-amino-4-fluorophenyl)cyclopropyl]acetateHCID 58288396(2S,3R)-2-(4-chlorophenyl)-4,4,4-trifluoro-3-methylbutanoic acid

Produkt 1

HCID 86719143Methyl [1-(3-{[(2S,3R)-2-(4-chlorophenyl)-4,4,4-trifluoro-3-methylbutanoyl]amino}-4-fluorophenyl)cyclopropyl]acetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 70 mg (0.31 mmol) of (2S,3R)-2-(4-chlorophenyl)-4,4,4-trifluoro-3-methylbutanoic acid, 84 mg (0.31 mmol) of methyl [1-(3-amino-4-fluorophenyl)cyclopropyl]acetate, 179 mg (0.47 mmol) of 2-(1H-7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (HATU) and 0.6 ml of pyridine in 2.4 ml of DMF was stirred at room temperature overnight. After the reaction had ended, the mixture was separated directly, without further work-up, by preparative HPLC. This gave 106 mg (0.22 mmol, 72% of theory) of the title compound as a colourless oil.

Aufarbeitung

  1. customthe mixture was separated directly, without further work-up, by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-d3a7cea8f4fe4158b332a4a740daa771
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09018414B2

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