1,1'-Carbonyldiimidazole → NGB 2904 hydrochloride

HRID 850143

Reaktionsgleichung

Reaktionsgleichung von HRID 850143
[CH:1]1[C:13]2[CH2:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][C:2]=1[C:14](O)=[O:15].C(N1C=CN=C1)(N1C=CN=C1)=O.[Cl:29][C:30]1[C:35]([Cl:36])=[CH:34][CH:33]=[CH:32][C:31]=1[N:37]1[CH2:42][CH2:41][N:40]([CH2:43][CH2:44][CH2:45][CH2:46][NH2:47])[CH2:39][CH2:38]1>O1CCCC1>[ClH:29].[Cl:29][C:30]1[C:35]([Cl:36])=[CH:34][CH:33]=[CH:32][C:31]=1[N:37]1[CH2:38][CH2:39][N:40]([CH2:43][CH2:44][CH2:45][CH2:46][NH:47][C:14]([C:2]2[CH:3]=[CH:4][C:5]3[C:6]4[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=4)[CH2:12][C:13]=3[CH:1]=2)=[O:15])[CH2:41][CH2:42]1

Komponenten

5

Edukt 3

HCID 682631,1'-CarbonyldiimidazoleHCID 3485919H-fluorene-2-carboxylic acidHCID 110986691-Piperazinebutanamine, 4-(2,3-dichlorophenyl)-

Produkt 1

HCID 19366304NGB 2904 hydrochlorideAusbeute 139,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A mixture of 9H-fluorene-2-carboxylic acid (100 mg, 0.48 mmol) and 1.1'-carbonyldiimidazole (80 mg, 0.5 mmol) in 10 mL of anhydrous tetrahydrofuran was stirred for 8 hours. A solution of 4-[4-(2,3-dichlorophenyl)-1-piperazinyl]-1-aminobutane (150 mg, 0.5 mmol) in 1 mL of tetrahydrofuran was added and the resulting mixture was stirred for 30 minutes. The reaction mixture was partitioned between ethyl acetate and water. The organic layer was washed with aqueous Na2CO3 solution, dried (Na2SO4) and concentrated in vacuo to give the title compound (185 mg, 78%). Hydrochloride salt was prepared by treating the free base with a solution of hydrogen chloride in ethyl acetate (mp 262-4° C.).

Aufarbeitung

  1. stirringthe resulting mixture was stirred for 30 minutes
  2. customThe reaction mixture was partitioned between ethyl acetate and water
  3. washThe organic layer was washed with aqueous Na2CO3 solution
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-2492c9d164984b47b86e64cff738f390
Quelldatensatz
uspto-grants-2000_01
Patentnummer
US06015900

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