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Isopropylamine → 6-{5-[(Cyclopropylamino)carbonyl]-2-methylphenyl}-N-isopropylphthalazine-1-carboxamide

HRID 2357630
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2357630
[C:1]([C:3]1[C:12]2[C:7](=[CH:8][C:9]([C:13]3[CH:14]=[C:15]([CH:22]=[CH:23][C:24]=3[CH3:25])[C:16]([NH:18][CH:19]3[CH2:21][CH2:20]3)=[O:17])=[CH:10][CH:11]=2)[CH:6]=[N:5][N:4]=1)#[N:2].[OH-:26].[K+].CN(C(ON1N=N[C:38]2[CH:39]=CC=N[C:37]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N)(C)C>C(O)C.O.C(OCC)(=O)C>[CH:19]1([NH:18][C:16]([C:15]2[CH:22]=[CH:23][C:24]([CH3:25])=[C:13]([C:9]3[CH:8]=[C:7]4[C:12](=[CH:11][CH:10]=3)[C:3]([C:1]([NH:2][CH:38]([CH3:39])[CH3:37])=[O:26])=[N:4][N:5]=[CH:6]4)[CH:14]=2)=[O:17])[CH2:20][CH2:21]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 6363IsopropylamineHCID 14797Potassium HydroxideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)2×HCID 68452746HCID 68452746, Verbindung

Produkt 1

HCID 684556306-{5-[(Cyclopropylamino)carbonyl]-2-methylphenyl}-N-isopropylphthalazine-1-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8857Ethyl AcetateLösungsmittelHCID 19096565Water ethanolLösungsmittel

Versuchsvorschrift

3-(1-Cyanophthalazin-6-yl)-N-cyclopropyl-4-methylbenzamide (115 mg, 350 μmol) and potassium hydroxide (39 mg, 700 μmol) were dissolved in ethanol/water (1:1) (3.50 mL) before it was placed in the microwave for 10 min at 120° C. The reaction mixture was concentrated before it was dissolved in dimethylformamide (700 μl); HATU (266 mg, 700 μmol) and isopropylamine (150 μl, 1751 μmol) were added. This was stirred at RT for 16 h before more HATU was added, and the reaction mixture was stirred at RT for 7 h. The reaction mixture was diluted with 100 mL of ethyl acetate, added to a separatory funnel, partitioned with water, washed 2× with 50 mL of water, separated, dried over sodium sulfate, concentrated in vacuo, and purified by HPLC to give the title compound.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated before it
  2. dissolutionwas dissolved in dimethylformamide (700 μl)
  3. additionwas added
  4. additionadded to a separatory funnel
  5. custompartitioned with water
  6. washwashed 2× with 50 mL of water
  7. customseparated
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated in vacuo
  10. custompurified by HPLC

Quellen und Nachweise

ORD-Eintrag
ord-7787cc5079e646c0a36830e81bb265de
Quelldatensatz
uspto-grants-2010_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07759337B2

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