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Potassium Iodide → Ammonia

HRID 1433273
Notes
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Reaction equation

HRID 1433273 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[CH:5]=[C:6]([CH:40]=[CH:41][CH:42]=1)[O:7][CH2:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]([O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[C:14]([C@@H:16]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:17][CH2:18][N:19]([CH:23]([CH3:25])[CH3:24])[CH:20]([CH3:22])[CH3:21])[CH:15]=1.[I-].[K+].C(=O)([O-])O.[Na+].[CH2:50]([O:57][C:58]1[CH:63]=[CH:62][C:61]([C@@H:64]([O:67][Si:68]([C:71]([CH3:74])([CH3:73])[CH3:72])([CH3:70])[CH3:69])[CH2:65]Br)=[CH:60][C:59]=1[NH:75][S:76]([CH3:79])(=[O:78])=[O:77])[C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1.C(#N)CC>C(OCC)(=O)C.O>[NH3:1].[CH2:50]([O:57][C:58]1[CH:63]=[CH:62][C:61]([C@@H:64]([O:67][Si:68]([C:71]([CH3:72])([CH3:74])[CH3:73])([CH3:70])[CH3:69])[CH2:65][NH:1][CH2:2][CH2:3][C:4]2[CH:42]=[CH:41][CH:40]=[C:6]([O:7][CH2:8][CH2:9][C:10]3[CH:11]=[CH:12][C:13]([O:32][CH2:33][C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)=[C:14]([C@@H:16]([C:26]4[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=4)[CH2:17][CH2:18][N:19]([CH:20]([CH3:22])[CH3:21])[CH:23]([CH3:25])[CH3:24])[CH:15]=3)[CH:5]=2)=[CH:60][C:59]=1[NH:75][S:76]([CH3:79])(=[O:77])=[O:78])[C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 5

HCID 4875Potassium IodideHCID 7854PropionitrileHCID 516892Sodium BicarbonateHCID 46938715N-{2-(benzyloxy)-5-[(1R)-2-bromo-1-([tert-butyl(dimethyl)silyl]oxy}ethyl]phenyl}methanesulfonamideHCID 57933181(3R)-3-[5-{2-[3-(2-aminoethyl)phenoxy]ethyl}-2-(benzyloxy)phenyl]-N,N-diisopropyl-3-phenylpropan-1-amine

Product 2

HCID 222
Ammonia
HCID 57933179N-{2-(benzyloxy)-5-[(1R)-2-({2-[3-(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 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

(3R)-3-[5-{2-[3-(2-aminoethyl)phenoxy]ethyl}-2-(benzyloxy)phenyl]-N,N-diisopropyl-3-phenylpropan-1-amine (Preparation 38, 340 mg, 0.52 mmol), potassium iodide (86 mg, 0.52 mmol), sodium hydrogen carbonate (175 mg, 2.08 mmol) and N-{2-(benzyloxy)-5-[(1R)-2-bromo-1-{[tert-butyl(dimethyl)silyl]oxy}ethyl]phenyl}methanesulfonamide (Prepared according to WO2005/080324, 270 mg, 0.52 mmol) were added to propionitrile (5 ml) and stirred at 100° C. under nitrogen overnight. Mixture was cooled and water (100 ml) and ethyl acetate (100 ml) were added. Organics were separated and washed with brine (100 ml), 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 (100/0/0 to 85/15/1.5 by volume) to furnish the title compound as a glass, 257 mg.

Workup

  1. temperatureMixture was cooled
  2. customOrganics were separated
  3. washwashed with brine (100 ml)
  4. dry with materialdried (magnesium sulphate)
  5. customthe solvent removed in vacuo
  6. customThe residue was purified by column chromatography on silica gel eluting with dichloromethane

Sources & evidence

ORD record
ord-10357b07bbee43f4b1df4d53eebaa8f3
Source dataset
uspto-grants-2009_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07612084B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes