Potassium Sodium Tartrate → 2-chloro-N-(cyclopropylmethyl)-1-mesityl-N-propyl-6-(trifluoromethyl)-1H-imidazo[1,2-a]imidazole-5-carboxamide

HRID 1246317

Reaktionsgleichung

Reaktionsgleichung von HRID 1246317
[CH:1]1([CH2:4][NH:5][CH2:6][CH2:7][CH3:8])[CH2:3][CH2:2]1.C[Al](C)C.C([O:15][C:16]([C:18]1[N:22]2[CH:23]=[C:24]([Cl:35])[N:25]([C:26]3[C:31]([CH3:32])=[CH:30][C:29]([CH3:33])=[CH:28][C:27]=3[CH3:34])[C:21]2=[N:20][C:19]=1[C:36]([F:39])([F:38])[F:37])=O)C.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>C1(C)C=CC=CC=1>[CH:1]1([CH2:4][N:5]([CH2:6][CH2:7][CH3:8])[C:16]([C:18]2[N:22]3[CH:23]=[C:24]([Cl:35])[N:25]([C:26]4[C:27]([CH3:34])=[CH:28][C:29]([CH3:33])=[CH:30][C:31]=4[CH3:32])[C:21]3=[N:20][C:19]=2[C:36]([F:38])([F:37])[F:39])=[O:15])[CH2:3][CH2:2]1

Komponenten

6

Edukt 4

HCID 9357Potassium Sodium TartrateHCID 117787Cyclopropanemethanamine, N-propyl-HCID 16682925TrimethylaluminumHCID 207802236-Chloro-2-trifluoromethyl-7-(2,4,6-trimethyl-phenyl)-7H-imidazo[1,2-a]imidazole-3-carboxylic Acid Ethyl Ester

Produkt 1

HCID 207800092-chloro-N-(cyclopropylmethyl)-1-mesityl-N-propyl-6-(trifluoromethyl)-1H-imidazo[1,2-a]imidazole-5-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel3×

Versuchsvorschrift

To a solution of N-cyclopropylmethylpropylamine (0.22 mL, 1.530 mmol) in toluene (1.5 mL) at 0° C. was added 2.0M solution of trimethylaluminum in toluene (0.77 mL, 1.530 mmol). The clear solution was warmed to room temperature and stirred for 1 h. A solution of 6-chloro-2-trifluoromethyl-7-(2,4,6-trimethyl-phenyl)-7H-imidazo[1,2-a]imidazole-3-carboxylic acid ethyl ester (37.7 mg, 0.094 mmol) in toluene (1.0 mL) was added at 0° C. via cannula. The reaction mixture was heated at 80° C. for 2 h. A solution of Rochelle's salt (2.0 mL) was added carefully at 0° C. and the mixture was vigorously stirred for 30 min. The crude product was extracted with ethyl acetate. The combined organic extracts were dried with MgSO4. The solvent was removed under reduced pressure and the crude product was purified by a reverse-phase preparative HPLC. Yield—39.5 mg (90%). LC/MS: tR=1.93 min., MS: [M+H]=467.

Aufarbeitung

  1. temperatureThe reaction mixture was heated at 80° C. for 2 h
  2. stirringthe mixture was vigorously stirred for 30 min
  3. extractionThe crude product was extracted with ethyl acetate
  4. dry with materialThe combined organic extracts were dried with MgSO4
  5. customThe solvent was removed under reduced pressure
  6. customthe crude product was purified by a reverse-phase preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-e829fa74de1949ca842442fd11cf435d
Quelldatensatz
uspto-grants-2006_10
Patentnummer
US07125990B2

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