Potassium Iodide → Ammonia

HRID 1433257Notes

Reaction equation

HRID 1433257 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[CH:42]=[CH:41][C:7]([O:8][CH2:9][CH2:10][C:11]2[CH:12]=[CH:13][C:14]([O:33][CH2:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)=[C:15]([C@@H:17]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH2:18][CH2:19][N:20]([CH:24]([CH3:26])[CH3:25])[CH:21]([CH3:23])[CH3:22])[CH:16]=2)=[CH:6][CH:5]=1.[CH2:43]([O:50][C:51]1[CH:56]=[CH:55][C:54]([C@@H:57]([O:60][Si:61]([C:64]([CH3:67])([CH3:66])[CH3:65])([CH3:63])[CH3:62])[CH2:58]Br)=[CH:53][C:52]=1[NH:68][S:69]([CH3:72])(=[O:71])=[O:70])[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1.C(=O)([O-])O.[Na+].[I-].[K+]>C(#N)C>[NH3:1].[CH2:43]([O:50][C:51]1[CH:56]=[CH:55][C:54]([C@@H:57]([O:60][Si:61]([C:64]([CH3:65])([CH3:67])[CH3:66])([CH3:63])[CH3:62])[CH2:58][NH:1][CH2:2][CH2:3][C:4]2[CH:42]=[CH:41][C:7]([O:8][CH2:9][CH2:10][C:11]3[CH:12]=[CH:13][C:14]([O:33][CH2:34][C:35]4[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=4)=[C:15]([C@@H:17]([C:27]4[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=4)[CH2:18][CH2:19][N:20]([CH:24]([CH3:26])[CH3:25])[CH:21]([CH3:23])[CH3:22])[CH:16]=3)=[CH:6][CH:5]=2)=[CH:53][C:52]=1[NH:68][S:69]([CH3:72])(=[O:70])=[O:71])[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 516892Sodium BicarbonateHCID 46938715N-{2-(benzyloxy)-5-[(1R)-2-bromo-1-([tert-butyl(dimethyl)silyl]oxy}ethyl]phenyl}methanesulfonamideHCID 57933208(3R)-3-[5-{2-[4-(2-aminoethyl)phenoxy]ethyl}-2-(benzyloxy)phenyl]-N,N-diisopropyl-3-phenylpropan-1-amine

Product 2

HCID 222AmmoniaHCID 57933234N-{2-(benzyloxy)-5-[(1R)-2-({2-[4-(2-{4-(benzyloxy)-3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]phenyl}ethoxy)phenyl]ethyl}amino)-1-{[tert-butyl(dimethyl)silyl]oxy}ethyl]phenyl}methanesulfonamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

(3R)-3-[5-{2-[4-(2-aminoethyl)phenoxy]ethyl}-2-(benzyloxy)phenyl]-N,N-diisopropyl-3-phenylpropan-1-amine (Preparation 21, 95 mg, 0.17 mmol), N-{2-(benzyloxy)-5-[(1R)-2-bromo-1-{[tert-butyl(dimethyl)silyl]oxy}ethyl]phenyl}methanesulfonamide (WO2005/080324, 86 mg, 0.17 mmol), sodium hydrogen carbonate (42 mg, 0.51 mmol) and potassium iodide (28 mg, 0.17 mmol) were added to acetonitrile (2.5 ml) and heated to reflux for 24 hours, then cooled to room temperature and the solvents removed in vacuo, the residue was purified by column chromatography on silica gel eluting with dichloromethane:methanol:880 ammonia (2421810.8 to 95/5/0.5 by volume) to furnish the title compound as a white foam, 78 mg.

Workup

  1. temperatureheated
  2. temperatureto reflux for 24 hours
  3. customthe solvents removed in vacuo
  4. customthe residue was purified by column chromatography on silica gel eluting with dichloromethane

Sources & evidence

ORD record
ord-77129ac189504749a7eb9a365d0d7ae3
Source dataset
uspto-grants-2009_11
Patent number
US07612084B2

Reaction notes

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