Hydrochloric Acid → HCID 178509156, Verbindung

HRID 255001Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 255001
[NH2:1][CH2:2][C:3]1[C:4](=[N:9][NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[CH:12]=2)[C:5]([NH2:8])=[N:6][N:7]=1.C(N(CC)CC)C.[C:25]1(=[O:31])[O:30][C:28](=[O:29])[CH:27]=[CH:26]1.Cl>CN(C=O)C.C(OCC)(=O)C>[NH2:8][C:5]1[C:4](=[N:9][NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[CH:12]=2)[C:3]([CH2:2][NH:1][C:25]([CH:26]=[CH:27][C:28]([OH:30])=[O:29])=[O:31])=[N:7][N:6]=1

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 7923Maleic AnhydrideHCID 8471TriethylamineHCID 178510679HCID 178510679, Verbindung

Produkt 1

HCID 178509156HCID 178509156, VerbindungAusbeute 69,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

5-Aminomethyl-4-[(3-fluorophenyl)hydrazono]-4H-pyrazol-3-ylamine (60 mg, 0.25 mmole) was dissolved in 3 mL of anhydrous DMF. To this solution was added triethylamine (0.51 mmole, 52 mg) and then a solution of maleic anhydride (30.2 mg, 0.31 mmole) in 1 mL of DMF. The reaction mixture was stirred at ambient temperature for 30 minutes and then worked up by the addition of saline and ethyl acetate. The mixture was acidified with 1 mL of 1.5 M HCl. The aqueous phase was extracted with ethyl acetate. The combined organic layer was washed with saline three times and dried over anhydrous MgSO4. The solution was then filtered, concentrated and purified by preparative TLC (CH2Cl2:MeOH:trace acetic acid=6:1) to yield 58 mg of the title compound as a yellow powder. MS (m/z, ES−): 331 (M−1, 100%); 1H NMR (ppm, 300 MHz, DMSO-d6) □δ 11.90 (br s, 1H), 7.35-7.70 (m, 3H), 7.30 (br s, 2H), 6.12 (d, 1H), 5.70 (d, 1H), 4.52 (s, 2H).

Aufarbeitung

  1. extractionThe aqueous phase was extracted with ethyl acetate
  2. washThe combined organic layer was washed with saline three times
  3. dry with materialdried over anhydrous MgSO4
  4. filtrationThe solution was then filtered
  5. concentrationconcentrated
  6. custompurified by preparative TLC (CH2Cl2:MeOH:trace acetic acid=6:1)

Quellen und Nachweise

ORD-Eintrag
ord-2cc1dfe97ead4846b18c78deb40c361e
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07875728B2

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