Diisopropylethylamine → {3-(3-Isopropoxy-1,2,4-oxadiazol-5-yl)-5-[4-(trifluoromethoxy)phenyl]piperidin-1-yl}(thiomorpholin-4-yl)methanone

HRID 661286Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 661286
[N:1]1([C:7]([N:9]2[CH2:14][CH:13]([C:15]3[CH:20]=[CH:19][C:18]([O:21][C:22]([F:25])([F:24])[F:23])=[CH:17][CH:16]=3)[CH2:12][CH:11]([C:26]([OH:28])=O)[CH2:10]2)=[O:8])[CH2:6][CH2:5][S:4][CH2:3][CH2:2]1.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.O[N:63]=[C:64]([O:66][CH:67]([CH3:69])[CH3:68])[NH2:65]>CN(C=O)C>[CH:67]([O:66][C:64]1[N:65]=[C:26]([CH:11]2[CH2:12][CH:13]([C:15]3[CH:20]=[CH:19][C:18]([O:21][C:22]([F:25])([F:24])[F:23])=[CH:17][CH:16]=3)[CH2:14][N:9]([C:7]([N:1]3[CH2:2][CH2:3][S:4][CH2:5][CH2:6]3)=[O:8])[CH2:10]2)[O:28][N:63]=1)([CH3:69])[CH3:68]

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 581165811-(Thiomorpholin-4-ylcarbonyl)-5-[4-(trifluoromethoxy)phenyl]piperidine-3-carboxylic acidHCID 76225143isopropyl N-hydroxyimidocarbamate

Produkt 1

HCID 49819701{3-(3-Isopropoxy-1,2,4-oxadiazol-5-yl)-5-[4-(trifluoromethoxy)phenyl]piperidin-1-yl}(thiomorpholin-4-yl)methanone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

To a solution of 500 mg (1.20 mmol) of the carboxylic acid from Example 9A in 15.0 ml of DMF were added, at RT, 545 mg (1.43 mmol) of HATU and 0.46 ml (2.63 mmol) of N,N′-diisopropylethylamine, and the mixture was stirred for 30 min. Subsequently, the mixture was admixed with 565 mg (3.56 mmol; 75% purity) of isopropyl N′-hydroxyimidocarbamate [G. Zinner, G. Nebel, Arch. Pharm. 1970, 303, 385-390] and then stirred at RT for 2 h and at 120° C. for 2 h. The reaction solution was concentrated under reduced pressure and purified directly by means of preparative HPLC. Yield: 344 mg (58% of theory)

Aufarbeitung

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. custompurified directly by means of preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-5cfb31ecab954f37a3c47b5d8620318d
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08084469B2

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