Diisopropylethylamine → 1-(7,8-Bis(4-chlorophenyl)-3-oxo-2,3-dihydro-[1,2,4]triazolo[4,3-c]pyrimidin-5-yl)-3-(ethylamino)azetidine-3-carboxamide

HRID 271428Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 271428
[CH2:1]([NH:3][C:4]1([C:8]([NH2:10])=[O:9])[CH2:7][NH:6][CH2:5]1)[CH3:2].C(N(CC)C(C)C)(C)C.Cl[C:21]1[N:26]2[C:27](=[O:30])[NH:28][N:29]=[C:25]2[C:24]([C:31]2[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][CH:32]=2)=[C:23]([C:38]2[CH:43]=[CH:42][C:41]([Cl:44])=[CH:40][CH:39]=2)[N:22]=1>CCO>[Cl:44][C:41]1[CH:42]=[CH:43][C:38]([C:23]2[N:22]=[C:21]([N:6]3[CH2:7][C:4]([NH:3][CH2:1][CH3:2])([C:8]([NH2:10])=[O:9])[CH2:5]3)[N:26]3[C:27](=[O:30])[NH:28][N:29]=[C:25]3[C:24]=2[C:31]2[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][CH:32]=2)=[CH:39][CH:40]=1

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 11286531HCID 11286531, VerbindungHCID 587728405-chloro-7,8-bis(4-chlorophenyl)-[1,2,4]triazolo[4,3-c]pyrimidin-3(2H)-one

Produkt 1

HCID 587728451-(7,8-Bis(4-chlorophenyl)-3-oxo-2,3-dihydro-[1,2,4]triazolo[4,3-c]pyrimidin-5-yl)-3-(ethylamino)azetidine-3-carboxamideAusbeute 46,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a stirred suspension of 3-(ethylamino)azetidine-3-carboxamide (25 mg, 0.17 mmol) in EtOH (1.0 mL) at room temperature under argon was added N,N-diisopropylethylamine (60 mg, 0.46 mmol). The reaction mixture was stirred at room temperature for 10 min to obtain a clear solution to which was added 5-chloro-7,8-bis(4-chlorophenyl)-[1,2,4]triazolo[4,3-c]pyrimidin-3(2H)-one (60 mg, 0.15 mmol). The reaction mixture was stirred at 60° C. in a pre-heated oil bath for 5 min. The reaction mixture was then concentrated under reduced pressure, and the residue was dissolved in CH2Cl2 (5 mL). The resulting mixture was washed with water (2 mL×2), dried (MgSO4), and concentrated under reduced pressure to obtain the crude product. This crude product was purified by preparative reverse phase HPLC (without TFA) to obtain 35 mg of the title compound as a pale yellow solid. HPLC/MS: retention time=3.306 min, [M+H]30 =498.

Aufarbeitung

  1. customto obtain a clear solution to which
  2. stirringThe reaction mixture was stirred at 60° C. in a pre-heated oil bath for 5 min
  3. concentrationThe reaction mixture was then concentrated under reduced pressure
  4. dissolutionthe residue was dissolved in CH2Cl2 (5 mL)
  5. washThe resulting mixture was washed with water (2 mL×2)
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated under reduced pressure
  8. customto obtain the crude product
  9. customThis crude product was purified by preparative reverse phase HPLC (without TFA)

Quellen und Nachweise

ORD-Eintrag
ord-b9d90aaad47b4d07aae01cd12dc624c4
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07452892B2

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