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Lithium Hydroxide → HCID 68455974, Verbindung

HRID 2357653
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2357653
[C:1]([C:3]1[C:12]2[C:7](=[CH:8][C:9]([C:13]3[CH:14]=[C:15]([CH:20]=[CH:21][C:22]=3[CH3:23])[C:16](OC)=[O:17])=[CH:10][CH:11]=2)[CH:6]=[N:5][N:4]=1)#[N:2].[Li+].[OH-:25].CN(C(ON1N=NC2[CH:37]=[CH:38][CH:39]=[N:40]C1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C1(N)CC1>C1COCC1.O.C(OCC)(=O)C>[CH:39]1([NH:40][C:16]([C:15]2[CH:20]=[CH:21][C:22]([CH3:23])=[C:13]([C:9]3[CH:8]=[C:7]4[C:12](=[CH:11][CH:10]=3)[C:3]([C:1]([NH2:2])=[O:25])=[N:4][N:5]=[CH:6]4)[CH:14]=2)=[O:17])[CH2:37][CH2:38]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 3939Lithium HydroxideHCID 69828CyclopropylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 68455479HCID 68455479, Verbindung

Produkt 1

HCID 68455974HCID 68455974, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8857Ethyl AcetateLösungsmittelHCID 21881883Oxolane--water (1/1)Lösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

Methyl 3-(1-cyanophthalazin-6-yl)-4-methylbenzoate (120 mg, 396 μmol) was dissolved in THF/water (4:1) (3.96 mL) and LiOH (19 mg, 791 μmol) was added. The reaction mixture was stirred at 50° C. for 5.5 h, concentrated, and lyophilyzed under house vacuum. The reaction mixture was dissolved in DMF (791 μl) and HATU (301 mg, 791 μmol) and cyclopropylamine (277 μl, 3956 μmol) were added and the mixture was stirred at RT for 16 h. The mixture was diluted with 100 mL ethyl acetate, and partitioned with sodium bicarbonate (saturated, aqueous). The organic layers were washed 3×20 mL with sodium bicarbonate (saturated, aqueous), separated, dried over sodium sulfate, concentrated in vacuo, and purified by HPLC to give the title compound. MS (ES+): 347 (M+H)+.

Aufarbeitung

  1. concentrationconcentrated
  2. dissolutionThe reaction mixture was dissolved in DMF (791 μl)
  3. stirringthe mixture was stirred at RT for 16 h
  4. custompartitioned with sodium bicarbonate (saturated, aqueous)
  5. washThe organic layers were washed 3×20 mL with sodium bicarbonate (saturated, aqueous)
  6. customseparated
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated in vacuo
  9. custompurified by HPLC

Quellen und Nachweise

ORD-Eintrag
ord-ca0fd3987ace4388b1ac43beffeef1bd
Quelldatensatz
uspto-grants-2010_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07759337B2

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