Oxalyl chloride → HCID 178480676, Verbindung

HRID 16726

Reaktionsgleichung

Reaktionsgleichung von HRID 16726
C(Cl)(=O)C(Cl)=O.[CH3:7][N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:22]=[CH:21][C:17]([C:18]([OH:20])=O)=[CH:16][CH:15]=2)[CH2:10][CH2:9]1.CCN(C(C)C)C(C)C.[CH2:32]([C:40]1[CH:41]=[C:42]([NH2:45])[NH:43][N:44]=1)[CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>C(Cl)Cl>[CH3:7][N:8]1[CH2:9][CH2:10][N:11]([C:14]2[CH:15]=[CH:16][C:17]([C:18]([NH:45][C:42]3[NH:43][N:44]=[C:40]([CH2:32][CH2:33][C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)[CH:41]=3)=[O:20])=[CH:21][CH:22]=2)[CH2:12][CH2:13]1

Komponenten

7

Edukt 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 7365324-(4-Methylpiperazin-1-yl)benzoic acidHCID 1785075235-(2-Phenylethyl)-1H-pyrazol-3-amine

Produkt 1

HCID 178480676HCID 178480676, VerbindungAusbeute 4,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Oxalyl chloride (2M in DCM, 250 μl, 0.50 mmol, 1.1 eq) was added dropwise to a mixture of 4-(4-methylpiperazin-1-yl)benzoic acid (100 mg, 0.45 mmol, 1 eq) in DCM (5 ml, containing a few drops of DMF) and DIPEA (171 μl, 0.95 mmol, 2.1 eq) at O° C. After stirring for 1 h at 0° C., a solution of 5-phenethyl-2H-pyrazol-3-amine (128 mg, 0.68 mmol, 1.5 eq) in DCM (2 ml) was added dropwise. The mixture was maintained at 0° C. for 2 h, then gradually allowed to warm to room temperature overnight. The mixture was diluted with DCM (50 ml), washed with aq. NaHCO3 solution (50 ml) and the aqueous layer was extracted with DCM (50 ml). The combined organic layers were concentrated. The crude product was purified by reverse-phase prep. HPLC (basic) using a 30-50% gradient of acetonitrile in water (containing 1% ammonium hydroxide) to yield the title compound (8 mg, 3% yield).

Aufarbeitung

  1. temperatureThe mixture was maintained at 0° C. for 2 h
  2. temperatureto warm to room temperature overnight
  3. washwashed with aq. NaHCO3 solution (50 ml)
  4. extractionthe aqueous layer was extracted with DCM (50 ml)
  5. concentrationThe combined organic layers were concentrated
  6. customThe crude product was purified by reverse-phase prep

Quellen und Nachweise

ORD-Eintrag
ord-497ee524cd6c46a081af0d4567cf7fca
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07737149B2

Verknüpfte Notizen

Wird geladen…