Diisopropylethylamine → N-cyclopropyl-4-methyl-3-(7-(3-oxopiperazin-1-yl)thieno[2,3-d]pyridazin-2-yl)benzamide

HRID 19585

Reaktionsgleichung

Reaktionsgleichung von HRID 19585
Cl[C:2]1[N:3]=[N:4][CH:5]=[C:6]2[CH:10]=[C:9]([C:11]3[CH:12]=[C:13]([CH:20]=[CH:21][C:22]=3[CH3:23])[C:14]([NH:16][CH:17]3[CH2:19][CH2:18]3)=[O:15])[S:8][C:7]=12.[NH:24]1[CH2:29][CH2:28][NH:27][CH2:26][C:25]1=[O:30].C(N(CC)C(C)C)(C)C>CN1C(=O)CCC1.O>[CH:17]1([NH:16][C:14](=[O:15])[C:13]2[CH:20]=[CH:21][C:22]([CH3:23])=[C:11]([C:9]3[S:8][C:7]4=[C:2]([N:27]5[CH2:28][CH2:29][NH:24][C:25](=[O:30])[CH2:26]5)[N:3]=[N:4][CH:5]=[C:6]4[CH:10]=3)[CH:12]=2)[CH2:19][CH2:18]1

Komponenten

6

Edukt 3

HCID 81531DiisopropylethylamineHCID 231360Piperazin-2-oneHCID 866181933-(7-chlorothieno[2,3-d]pyridazin-2-yl)-N-cyclopropyl-4-methylbenzamide

Produkt 1

HCID 68559163N-cyclopropyl-4-methyl-3-(7-(3-oxopiperazin-1-yl)thieno[2,3-d]pyridazin-2-yl)benzamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Reaktionsbedingungen

Temperatur
180 °C

Versuchsvorschrift

The title compound was prepared by a method similar to that described in Example 2. 3-(7-chlorothieno[2,3-d]pyridazin-2-yl)-N-cyclopropyl-4-methylbenzamide (100 mg, 291 μmol), piperazin-2-one (44 mg, 436 μmol) and N,N-diisopropylethylamine (152 μl, 873 μmol) were combined in NMP (2 ml) and heated to 180° C. for 18 hrs. The mixture was cooled to RT, diluted with H2O and filtered. The solids were washed with H2O and air-dried. Both the solid and solution were collected, dissolved in DMSO and purified with reverse-phase chromatography (Phenomenex Synergi 4m Max RP 80 A column, 150×21 mm, 20 ml/min, 10-95% CH3CN/H2O, 0.1% TFA, 10.5 min gradient). The residue was purified with reverse-phase chromatography (Phenomenex Synergi 4m Max RP 80 A column, 150×21 mm, 20 ml/min, 10-95% CH3CN/H2O, 0.1% TFA, 10.5 min gradient) to afford the title compound. MS (ESI, pos. ion) m/z: 408 (M+1).

Aufarbeitung

  1. customThe title compound was prepared by a method similar to
  2. temperatureThe mixture was cooled to RT
  3. filtrationfiltered
  4. washThe solids were washed with H2O
  5. customair-dried
  6. customBoth the solid and solution were collected
  7. dissolutiondissolved in DMSO
  8. custompurified with reverse-phase chromatography (Phenomenex Synergi 4m Max RP 80 A column, 150×21 mm, 20 ml/min, 10-95% CH3CN/H2O, 0.1% TFA, 10.5 min gradient)
  9. customThe residue was purified with reverse-phase chromatography (Phenomenex Synergi 4m Max RP 80 A column, 150×21 mm, 20 ml/min, 10-95% CH3CN/H2O, 0.1% TFA, 10.5 min gradient)

Quellen und Nachweise

ORD-Eintrag
ord-409c0590403f4f26a9b46990c872994d
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07745449B2

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