Oxalyl chloride → 2-Morpholinoethyl 4-(1,4-dihydroindeno[1,2-c]pyrazol-3-yl)-benzoate

HRID 990998Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 990998
[N:1]1([C:13]2C=CC(C(Cl)=O)=C[CH:14]=2)[C:5]2C3C(C[C:4]=2C=N1)=CC=CC=3.[NH:22]1[C:26]2[C:27]3[C:32]([CH2:33][C:25]=2[C:24]([C:34]2[CH:42]=[CH:41][C:37]([C:38]([OH:40])=[O:39])=[CH:36][CH:35]=2)=[N:23]1)=[CH:31][CH:30]=[CH:29][CH:28]=3.[C:43](Cl)(=[O:47])[C:44](Cl)=O>ClCCl.CN(C=O)C>[NH:22]1[C:26]2[C:27]3[C:32]([CH2:33][C:25]=2[C:24]([C:34]2[CH:42]=[CH:41][C:37]([C:38]([O:40][CH2:4][CH2:5][N:1]4[CH2:44][CH2:43][O:47][CH2:14][CH2:13]4)=[O:39])=[CH:36][CH:35]=2)=[N:23]1)=[CH:31][CH:30]=[CH:29][CH:28]=3

Komponenten

6

Edukt 3

HCID 65578Oxalyl chlorideHCID 184158474-(1,4-Dihydroindeno[1,2-c]pyrazol-3-yl)benzoic acidHCID 538774994-(1,4-Dihydroindeno[1,2-c]pyrazol-yl)benzoyl chloride

Produkt 1

HCID 184159982-Morpholinoethyl 4-(1,4-dihydroindeno[1,2-c]pyrazol-3-yl)-benzoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of 4-(1,4-dihydroindeno[1,2-c]pyrazol-yl)benzoyl chloride [(500 mg) prepared by reaction of the product of Example 8 (1.45 g) with oxalyl chloride (1.5 ml) in dichloromethane (100 ml) and DMF (8 drops) followed by evaporation of the solvent], dichloromethane (50 ml), 2-morpholinoethanol (0.22 ml) and triethylamine (0.5 ml) was stirred at ambient temperature for 3.5 hours. The mixture was washed with water then with saturated sodium bicarbonate solution, then dried, filtered and evaporated to give an oil which was purified by flash column chromatography on silica using dichloromethane/IMS (10:1) as the mobile phase to give an oil which was purified again by flash column chromatography using dichloromethane/IMS (25:1) as the mobile phase to give the product 2-morpholinoethyl 4-(1,4-dihydroindeno[1,2-c]pyrazol-3-yl)- benzoate as a solid, m.p. 168-172° C.

Aufarbeitung

  1. customfollowed by evaporation of the solvent], dichloromethane (50 ml), 2-morpholinoethanol (0.22 ml) and triethylamine (0.5 ml)
  2. washThe mixture was washed with water
  3. dry with materialwith saturated sodium bicarbonate solution, then dried
  4. filtrationfiltered
  5. customevaporated
  6. customto give an oil which
  7. customwas purified by flash column chromatography on silica
  8. customto give an oil which
  9. customwas purified again by flash column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-60df7400a7a24ef7b22ae86094068b08
Quelldatensatz
uspto-grants-2002_10
Patentnummer
US06462036B1

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