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Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → (4,4-Difluoro-azepan-1-yl)-(5-phenyl-thiophen-3-yl)-methanone

HRID 1914591
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1914591
[C:1]1([C:7]2[S:11][CH:10]=[C:9]([C:12]([OH:14])=O)[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[F:16][C:17]1([F:24])[CH2:23][CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C(#N)C>[F:16][C:17]1([F:24])[CH2:23][CH2:22][CH2:21][N:20]([C:12]([C:9]2[CH:8]=[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[S:11][CH:10]=2)=[O:14])[CH2:19][CH2:18]1
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Komponenten

5

Edukt 3

HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 162272215-Phenylthiophene-3-carboxylic acidHCID 569243114,4-Difluoroazepane hydrochloride

Produkt 1

HCID 44226682(4,4-Difluoro-azepan-1-yl)-(5-phenyl-thiophen-3-yl)-methanoneAusbeute 42 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342
Acetonitrile
Lösungsmittel

Versuchsvorschrift

5-Phenyl-thiophene-3-carboxylic acid (0.20 g, 1.11 mmol) and 4,4-difluoro-azepane hydrochloride (0.19 g, 1.11 mmol) were stirred in acetonitrile (10 mL) with silica-supported diethylamine (1.32 mmol/g, 2.5 g) and HATU (0.40 g, 1.11 mmol) for 18 hours. The reaction mixture was filtered and the solvent was removed by evaporation then the crude material was purified by HPLC, eluting with 10%-98% acetonitrile in water (0.1% formic acid) over 20 minutes. The fractions containing the desired product were evaporated to give the title compound as a gum (0.15 g). LCMS m/z 322.19 [M+H]+ R.T.=11.14 min (Analytical Method 2).

Aufarbeitung

  1. filtrationThe reaction mixture was filtered
  2. customthe solvent was removed by evaporation
  3. customthe crude material was purified by HPLC
  4. washeluting with 10%-98% acetonitrile in water (0.1% formic acid) over 20 minutes
  5. additionThe fractions containing the desired product
  6. customwere evaporated

Quellen und Nachweise

ORD-Eintrag
ord-ae6a2e4df26445c8bcb3e58312c4873b
Quelldatensatz
uspto-grants-2013_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08614209B2

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