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Ethyl Acetate → HCID 60141904, Verbindung

HRID 1805269
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1805269
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[C:13]([C:14]([OH:16])=O)=[C:12]([C:17]2[CH:18]=[N:19][N:20]([C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([Cl:32])[CH:27]=3)[C:21]=2[C:22]([F:25])([F:24])[F:23])[O:11][N:10]=1.[CH3:33][NH:34][O:35][CH3:36].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(OC(=O)C)C>CN(C)O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[C:13]([C:14]([N:34]([O:35][CH3:36])[CH3:33])=[O:16])=[C:12]([C:17]2[CH:18]=[N:19][N:20]([C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([Cl:32])[CH:27]=3)[C:21]=2[C:22]([F:24])([F:25])[F:23])[O:11][N:10]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 8857Ethyl AcetateHCID 14232N,O-DimethylhydroxylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86668506HCID 86668506, Verbindung

Produkt 1

HCID 60141904HCID 60141904, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 27970DimethylhydroxylamineLösungsmittel

Versuchsvorschrift

To a solution of 10.8 g (22.2 mmol) 3-(2-chloro-6-fluorophenyl)-5-(1-(3-chlorophenyl)-5-(trifluoromethyl)-1H-pyrazol-4-yl)isoxazole-4-carboxylic acid, 2.17 g (1 eq) N,O-Dimethylhydroxylamine and 8.42 g (1 eq) HBTU in dimethylhydroxylamine 3.68 mL DIPEA were added. The mixture was stirred overnight at r.t. The solvent was removed in the vacuum. The residue was resolved in ethylacetate and extracted with sodium hydrogen carbonate (5%, aq) and citric acid (5%, aq). The organic layer was dried over anhydrous magnesium sulfate and the solvent was removed in the vacuum. TLC (6:4 petrolether:ethylacetate) showed residual educt. The product was isolated by column chromatoghraphy (6:4) petrolether:ethylacetate). The product (example I-63) was dried under vacuum to yield 2.28 g (19%). Result of LC/MS MH+: 528.8; 1H NMR (DMSO-d6; CCl4): 3.08 (3H, s, CH3), 3.36 (3H, s, CH3), 7.40-7.81 (7H, m, CH-arom.), 8.39 (1H, s, CH-pyraz.)

Aufarbeitung

  1. customThe solvent was removed in the vacuum
  2. extractionextracted with sodium hydrogen carbonate (5%, aq) and citric acid (5%, aq)
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. customthe solvent was removed in the vacuum
  5. customThe product was isolated by column chromatoghraphy (6:4) petrolether
  6. customto yield 2.28 g (19%)
  7. customResult of LC/MS MH+

Quellen und Nachweise

ORD-Eintrag
ord-c5528dd46e9341bba55ec1830cd108b9
Quelldatensatz
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08354436B2

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