Potassium Iodide → Ammonia

HRID 1433250노트

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HRID 1433250 반응식
Cl.Cl.[NH2:3][CH2:4][CH2:5][C:6]1[CH:39]=[CH:38][C:9]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[C:17]([C@@H:22]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[CH2:23][CH2:24][N:25]([CH:29]([CH3:31])[CH3:30])[CH:26]([CH3:28])[CH3:27])[CH:16]=2)=[CH:8][CH:7]=1.[CH2:40]([O:47][C:48]1[CH:53]=[CH:52][C:51]([C@@H:54]([O:57][Si:58]([C:61]([CH3:64])([CH3:63])[CH3:62])([CH3:60])[CH3:59])[CH2:55]Br)=[CH:50][C:49]=1[NH:65][S:66]([CH3:69])(=[O:68])=[O:67])[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1.C(=O)([O-])O.[Na+].[I-].[K+]>O.C(#N)C>[NH3:3].[CH2:40]([O:47][C:48]1[CH:53]=[CH:52][C:51]([C@@H:54]([O:57][Si:58]([C:61]([CH3:62])([CH3:64])[CH3:63])([CH3:60])[CH3:59])[CH2:55][NH:3][CH2:4][CH2:5][C:6]2[CH:7]=[CH:8][C:9]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]3[CH:20]=[CH:19][C:18]([OH:21])=[C:17]([C@@H:22]([C:32]4[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=4)[CH2:23][CH2:24][N:25]([CH:26]([CH3:28])[CH3:27])[CH:29]([CH3:30])[CH3:31])[CH:16]=3)=[CH:38][CH:39]=2)=[CH:50][C:49]=1[NH:65][S:66]([CH3:69])(=[O:67])=[O:68])[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1

참가 물질

8

반응물 4

HCID 4875Potassium IodideHCID 516892Sodium BicarbonateHCID 46938715N-{2-(benzyloxy)-5-[(1R)-2-bromo-1-([tert-butyl(dimethyl)silyl]oxy}ethyl]phenyl}methanesulfonamideHCID 866164804-{4-[4-(2-Aminoethyl)phenoxy]butyl}-2-[(1R)-3-(diisopropylamino)-1-phenylpropyl]phenol bis hydrochloride salt

생성물 2

HCID 222AmmoniaHCID 57933232N-{2-(Benzyloxy)-5-[(1R)-1-{[tert-butyl(dimethyl)silyl]oxy}-2-({2-[4-(4-{3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]-4-hydroxyphenyl}butoxy)phenyl]ethyl}amino)ethyl]phenyl}methanesulfonamide

시약·촉매·용매 2

HCID 962Water용매HCID 6342Acetonitrile용매

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온도
90 °C

실험 절차

4-{4-[4-(2-aminoethyl)phenoxy]butyl}-2-[(1R)-3-(diisopropylamino)-1-phenylpropyl]phenol bis hydrochloride salt (Preparation 13, 420 mg, 0.73 mmol), N-{2-(benzyloxy)-5-[(1R)-2-bromo-1-{[tert-butyl(dimethyl)silyl]oxy}ethyl]phenyl}methanesulfonamide (Prepared according to WO2005/080324, 375 mg, 0.73 mmol), sodium hydrogen carbonate (245 mg, 2.92 mmol) and potassium iodide (121 mg, 0.73 mmol) were added to acetonitrile (15 ml) and heated to 90° C. for 30 minutes and left at room temperature for 48 hours, water was added and extracted with ethyl acetate, dried (magnesium sulphate) and the solvent removed in vacuo, the residue was purified by column chromatography on silica gel eluting with dichloromethane:methanol:880 ammonia (971310.3 to 92/810.8 by volume) to furnish the title compound as a white foam, 207 mg.

후처리

  1. extractionextracted with ethyl acetate
  2. dry with materialdried (magnesium sulphate)
  3. customthe solvent removed in vacuo
  4. customthe residue was purified by column chromatography on silica gel eluting with dichloromethane

출처 및 근거

ORD 기록
ord-cdee056ef52248b4bb45571a676bef36
출처 데이터셋
uspto-grants-2009_11
특허 번호
US07612084B2

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