Xanthene-9-carboxylic acid → N-[9-(cyclooctylmethyl)-9-azabicyclo[3.3.1]nonan-3-yl]xanthene-9-carboxamide

HRID 370271

Reaktionsgleichung

Reaktionsgleichung von HRID 370271
[NH2:1][CH:2]1[CH2:9][CH:8]2[N:10]([C:11](OC(C)(C)C)=O)[CH:4]([CH2:5][CH2:6][CH2:7]2)[CH2:3]1.[CH:18]1[C:31]2[CH:30]([C:32]([OH:34])=O)[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[O:23][C:22]=2[CH:21]=[CH:20][CH:19]=1.CCN=C=N[CH2:40][CH2:41][CH2:42]N(C)C.Cl.ON1[C:52]2[CH:53]=C[CH:55]=[CH:56][C:51]=2N=N1>O.CN(C)C=O>[CH:40]1([CH2:11][N:10]2[CH:4]3[CH2:5][CH2:6][CH2:7][CH:8]2[CH2:9][CH:2]([NH:1][C:32]([CH:30]2[C:31]4[CH:18]=[CH:19][CH:20]=[CH:21][C:22]=4[O:23][C:24]4[C:29]2=[CH:28][CH:27]=[CH:26][CH:25]=4)=[O:34])[CH2:3]3)[CH2:41][CH2:42][CH2:55][CH2:56][CH2:51][CH2:52][CH2:53]1

Komponenten

7

Edukt 4

HCID 65736Xanthene-9-carboxylic acidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 23283006Tert-butyl 3-amino-9-azabicyclo[3.3.1]nonane-9-carboxylate

Produkt 1

HCID 15480669N-[9-(cyclooctylmethyl)-9-azabicyclo[3.3.1]nonan-3-yl]xanthene-9-carboxamideAusbeute 92,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

15 ml of anhydrous N,N-dimethylformamide suspension having 165 mg of 3-amino-9-t-butoxycarbonyl-9-azabicyclo[3.3.1]nonane and 155 mg of xanthene-9-carboxylic acid was cooled with ice, and 224 mg of EDCI.HCl and 157 mg of 1-hydroxybenzotriazole were successively added thereto. The temperature was raised to room temperature immediately, and the reaction mixture was stirred for 21 hours. 10 ml of water was added to the reaction solution, followed by extraction with diethyl ether. The organic layer was washed with 10% citric acid solution, saturated aqueous sodium bicarbonate, water and saturated aqueous sodium chloride, followed by drying over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and 301 mg of the title compound as a white solid was obtained.

Aufarbeitung

  1. additionwere successively added
  2. extractionfollowed by extraction with diethyl ether
  3. washThe organic layer was washed with 10% citric acid solution, saturated aqueous sodium bicarbonate, water and saturated aqueous sodium chloride
  4. dry with materialby drying over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-37a5a51b4e0a4336a8ee8e83cf8c5826
Quelldatensatz
uspto-grants-2000_10
Patentnummer
US06140338

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