Potassium Iodide → Ammonia

HRID 1433250Notes

Reaction equation

HRID 1433250 reaction equation
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

Participants

8

Reactant 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

Product 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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
90 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-cdee056ef52248b4bb45571a676bef36
Source dataset
uspto-grants-2009_11
Patent number
US07612084B2

Reaction notes

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