Potassium Carbonate → N-{2-[7-(2-Cyano-benzyl)-9-oxa-3,7-diaza-bicyclo[3.3.1]non-3-yl]-ethyl}-N-[2-(4-cyano-phenoxy)-ethyl]-methanesulfonamide

HRID 899156Notes

Reaction equation

HRID 899156 reaction equation
[C:1]([C:3]1[CH:27]=[CH:26][C:6]([O:7][CH2:8][CH2:9][N:10]([CH2:15][CH2:16][N:17]2[CH2:24][CH:23]3[O:25][CH:19]([CH2:20][NH:21][CH2:22]3)[CH2:18]2)[S:11]([CH3:14])(=[O:13])=[O:12])=[CH:5][CH:4]=1)#[N:2].Br[C:29]1[C:36](C)=[CH:35][CH:34]=[CH:33][C:30]=1[C:31]#[N:32].[C:38](=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:31]([C:30]1[CH:33]=[CH:34][CH:35]=[CH:36][C:29]=1[CH2:38][N:21]1[CH2:22][CH:23]2[O:25][CH:19]([CH2:18][N:17]([CH2:16][CH2:15][N:10]([CH2:9][CH2:8][O:7][C:6]3[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:27][CH:26]=3)[S:11]([CH3:14])(=[O:13])=[O:12])[CH2:24]2)[CH2:20]1)#[N:32]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 154691152-Bromo-3-methylbenzonitrileHCID 69072689N-[2-(4-Cyanophenoxy)ethyl]-N-[2-(9-oxa-3,7-diazabicyclo[3.3.1]non-3-yl)ethyl]methanesulfonamide

Product 1

HCID 11691965N-{2-[7-(2-Cyano-benzyl)-9-oxa-3,7-diaza-bicyclo[3.3.1]non-3-yl]-ethyl}-N-[2-(4-cyano-phenoxy)-ethyl]-methanesulfonamideYield 55.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
160 °C

Procedure

To N-[2-(4-cyano-phenoxy)-ethyl]-N-[2-(9-oxa-3,7-diaza-bicyclo[3.3.1]-non-3-yl)-ethyl]-methanesulfonamide (0.079 g, 0.20 mmol), 2-bromo-methyl-benzonitrile (0.041 g, 0.21 mmol) and anhydrous potassium carbonate (0.042 g, 0.30 mmol) was added dry acetonitrile (4 mL). The mixture was heated by microwave irradiation (15 minutes, 160° C.) and was then filtered. The filtrate was loaded onto a cation exchange column (SCX-2, Isolute™, 2 g). The column was washed with dichloromethane, acetonitrile and dichloromethane/methanol 80:20 before eluting the crude product with 20% methanol saturated with ammonia in dichloromethane. The filtrate was concentrated in vacuo and the crude product was purified by chromatography on silica gel using methanol saturated with ammonia in dichloromethane as eluent, which afforded 57 mg (55.9%) of the title compound.

Workup

  1. filtrationwas then filtered
  2. washThe column was washed with dichloromethane, acetonitrile and dichloromethane/methanol 80:20
  3. washbefore eluting the crude product with 20% methanol saturated with ammonia in dichloromethane
  4. concentrationThe filtrate was concentrated in vacuo
  5. customthe crude product was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-dfa9122a566f40459ded71abfe04f721
Source dataset
uspto-grants-2008_04
Patent number
US07354917B2

Reaction notes

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