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

HRID 370271

반응식

HRID 370271 반응식
[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

참가 물질

7

반응물 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

생성물 1

HCID 15480669N-[9-(cyclooctylmethyl)-9-azabicyclo[3.3.1]nonan-3-yl]xanthene-9-carboxamide수율 92.9%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-37a5a51b4e0a4336a8ee8e83cf8c5826
출처 데이터셋
uspto-grants-2000_10
특허 번호
US06140338

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