Citric Acid → 1-{1-[4-(4-amino-3,5-dibromophenyl)-1,4-dioxobutyl]-4-piperidinyl}-1,3-dihydro-4-phenyl-2(2H)-imidazolone

HRID 1766196Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1766196
[NH2:1][C:2]1[C:7]([Br:8])=[CH:6][C:5]([C:9](=[O:15])[CH2:10][CH2:11][C:12]([OH:14])=O)=[CH:4][C:3]=1[Br:16].[NH:17]1[CH2:22][CH2:21][CH:20]([N:23]2[CH:27]=[C:26]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[NH:25][C:24]2=[O:34])[CH2:19][CH2:18]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C.C(O)(=O)CC(CC(O)=O)(C(O)=O)O.[K+].[Br-].BrBr>O.O1CCCC1>[NH2:1][C:2]1[C:3]([Br:16])=[CH:4][C:5]([C:9](=[O:15])[CH2:10][CH2:11][C:12]([N:17]2[CH2:18][CH2:19][CH:20]([N:23]3[CH:27]=[C:26]([C:28]4[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=4)[NH:25][C:24]3=[O:34])[CH2:21][CH2:22]2)=[O:14])=[CH:6][C:7]=1[Br:8]

Komponenten

10

Edukt 7

HCID 311Citric AcidHCID 24408BromineHCID 81531DiisopropylethylamineHCID 253877Potassium BromideHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 11175554HCID 11175554, VerbindungHCID 113455464-Phenyl-1-(piperidin-4-yl)-1,3-dihydro-2H-imidazol-2-one

Produkt 1

HCID 98944161-{1-[4-(4-amino-3,5-dibromophenyl)-1,4-dioxobutyl]-4-piperidinyl}-1,3-dihydro-4-phenyl-2(2H)-imidazolone

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of 1.0 g (2.849 mmol) of 4-amino-3,5-dibromo-γ-oxo-benzenebutanoic acid, 1.04 g (2.91 mmol) of 1,3-dihydro-1-(4-piperidinyl)-4-phenyl-2(2H)-imidazolone, 0.935 g (2.912 mmol) of TBTU, 1.02 ml (5.77 mmol) of DIEA and 50 ml of tetrahydrofuran was stirred for 1 hour at ambient temperature. The reaction mixture was diluted with 300 ml of water and acidified slightly with citric acid. The precipitate formed was suction filtered and washed carefully with water, then with 3 ml of tetrahydrofuran, and finally dried in a circulating air dryer at a temperature of 60° C. 1.3 g (79% of theoretical) of a colourless, crystalline product were obtained, Rf 0.47 (El A). IR (KBr): 1679.9 cm−1 (C═O) MS: M+=574/576/578 (Br2)

Aufarbeitung

  1. customThe precipitate formed
  2. filtrationfiltered
  3. washwashed carefully with water
  4. dry with materialwith 3 ml of tetrahydrofuran, and finally dried in a circulating air dryer at a temperature of 60° C
  5. custom1.3 g (79% of theoretical) of a colourless, crystalline product were obtained

Quellen und Nachweise

ORD-Eintrag
ord-d58ad67c24ac41cbb83f7bce5ef521dd
Quelldatensatz
uspto-grants-2007_06
Patentnummer
US07230001B1

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