Diisopropylethylamine → HCID 54767443, Verbindung

HRID 1690279

Reaktionsgleichung

Reaktionsgleichung von HRID 1690279
[CH:1]1([C:4]2[CH:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:10]=[CH:9][C:5]=2[C:6]([OH:8])=O)[CH2:3][CH2:2]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)C(C)C)C.[CH3:50][N:51]1[CH:56]2[CH2:57][CH2:58][CH:52]1[C:53]([NH2:65])([C:59]1[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=1)[CH2:54][CH2:55]2>CN(C)C=O>[CH:1]1([C:4]2[CH:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:10]=[CH:9][C:5]=2[C:6]([NH:65][C:53]2([C:59]3[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=3)[CH2:54][CH2:55][CH:56]3[N:51]([CH3:50])[CH:52]2[CH2:58][CH2:57]3)=[O:8])[CH2:2][CH2:3]1

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 58565893(1RS,2RS,5SR)-8-Methyl-2-phenyl-8-aza-bicyclo[3.2.1]oct-2-ylamine2×HCID 594384852-Cyclopropyl-4-(trifluoromethyl)benzoic acid2×

Produkt 1

HCID 54767443HCID 54767443, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

To a solution of 23.4 mg (0.102 mmol) 2-cyclopropyl-4-trifluoromethyl-benzoic acid (intermediate B2), 53.1 mg (0.139 mmol) HATU and 64 ul (0.370 mmol) N-ethyldiisopropylamine in 0.8 ml N,N-dimethylformamide, was added a solution of 20 mg (0.0925 mmol) (1RS,2RS,5SR)-8-methyl-2-phenyl-8-aza-bicyclo[3.2.1]oct-2-ylamine (intermediate A1) in 0.2 ml N,N-dimethylformamide. The mixture was stirred at room temperature overnight. The solvent was removed in vacuo. The residue was dissolved in ethyl acetate. The solution was washed once with water and twice with a saturated sodium bicarbonate solution. The aqueous layer was extracted once with ethyl acetate. The combined extracts were dried over sodium sulfate, filtered and concentrated in vacuo. The crude oil was purified with flash column chromatography on silica (5 g) eluting with a gradient formed from n-heptane and ethyl acetate (0 to 50%) to provide 10 mg (y: 25.2%) of the title compound as a colorless viscous oil. MS (m/e): 429.2 (M+H+)

Aufarbeitung

  1. customThe solvent was removed in vacuo
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washThe solution was washed once with water and twice with a saturated sodium bicarbonate solution
  4. extractionThe aqueous layer was extracted once with ethyl acetate
  5. dry with materialThe combined extracts were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude oil was purified with flash column chromatography on silica (5 g)
  9. washeluting with a gradient
  10. customformed from n-heptane and ethyl acetate (0 to 50%)

Quellen und Nachweise

ORD-Eintrag
ord-4963ac3d45a24c9d97a38d18664bf482
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08153653B2

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