Dichloromethane → HCID 10019969, Verbindung

HRID 2375376Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2375376
[C:1]([C:4]1[CH:8]=[C:7]([CH3:9])[N:6]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][C:11]=2[O:18][CH3:19])[C:5]=1[CH3:20])(=O)[CH3:2].[CH2:21]1[CH:23]([C:24](Cl)=O)C1.[Sn](Cl)(Cl)(Cl)Cl.[CH2:32](Cl)Cl.[NH2:35][NH2:36]>C1(C)C=CC=CC=1.[OH-].[Na+].C(O)C.O>[CH:23]1([C:32]2[C:8]3=[C:7]([CH3:9])[N:6]([C:10]4[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][C:11]=4[O:18][CH3:19])[C:5]([CH3:20])=[C:4]3[C:1]([CH3:2])=[N:36][N:35]=2)[CH2:24][CH2:21]1

Komponenten

10

Edukt 5

HCID 6344DichloromethaneHCID 9321HydrazineHCID 24287Tin tetrachlorideHCID 77637Cyclopropanecarbonyl chlorideHCID 393723951-[1-(2,4-Dimethoxyphenyl)-2,5-dimethyl-1H-pyrrol-3-yl]ethan-1-one

Produkt 1

HCID 10019969HCID 10019969, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittelHCID 14798Sodium HydroxideLösungsmittel

Versuchsvorschrift

To a solution of 3-acetyl-1-(2,4-dimethoxyphenyl)-2,5-dimethylpyrrole (273 mg, 1.0 mmol) in toluene (5 mL) at −78° C. was added 3-cyclopropanecarbonyl chloride (0.11 mL, 1.2 mmol) followed by dropwise addition of a 1.0M solution of tin(IV) chloride in CH2Cl2 (1.2 mL, 1.2 mmol). The reaction was allowed to warm to room temp overnight. The solution was diluted with 0.25M NaOH, extracted with EtOAc, the organic layer washed with brine, dried over MgSO4, filtered, concentrated in vacuo, and purified by flash chromatography (10-25% EtOAc/hexanes) to give the dione (MS (ESI) 342 (M +H)+). The dione was taken up in ethanol (5 mL) and excess hydrazine (0.1 mL) was added. The solution was stirred at 40° C. overnight, poured into water, and filtered to give 1-(cyclopropyl)-6-(2,4-dimethoxyphenyl)-4,5,7-trimethyl-6H-pyrrolo[3,4-d]pyridazine as a white solid: 1H NMR (CDCl3, 500 MHz) δ 7.03 (dd, 1H), 6.66-6.56 (m, 2H), 3.90 (s, 3H), 3.75 (s, 3H), 2.75 (s, 3H), 2.47 (s, 3H), 2.39 (quintet, 1H), 2.38 (s, 3H), 1.35-1.28 (m, 2H), 0.97 (dd, 2H); MS (ESI) 338 (M+H)+.

Aufarbeitung

  1. extractionextracted with EtOAc
  2. washthe organic layer washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. custompurified by flash chromatography (10-25% EtOAc/hexanes)
  7. customto give the dione (MS (ESI) 342 (M +H)+)
  8. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-a5038d784d844652bf6f32dfc5a1bbff
Quelldatensatz
uspto-grants-2008_12
Patentnummer
US07465730B2

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