Potassium Carbonate → N-[2-(4-Cyanophenoxy)ethyl]-N-{2-[7-(4-fluorobenzyl)-9-oxa-3,7-diazabicyclo[3.3.1]non-3-yl]ethyl}methanesulfonamide

HRID 899149Notes

Reaction equation

HRID 899149 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[CH2:29][C:30]1[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=1.C([O-])([O-])=O.[K+].[K+]>>[C:1]([C:3]1[CH:4]=[CH:5][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][N:21]([CH2:29][C:30]4[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=4)[CH2:22]3)[CH2:18]2)[S:11]([CH3:14])(=[O:13])=[O:12])=[CH:26][CH:27]=1)#[N:2]

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 680214-Fluorobenzyl bromideHCID 69072689N-[2-(4-Cyanophenoxy)ethyl]-N-[2-(9-oxa-3,7-diazabicyclo[3.3.1]non-3-yl)ethyl]methanesulfonamide

Product 1

HCID 11677772N-[2-(4-Cyanophenoxy)ethyl]-N-{2-[7-(4-fluorobenzyl)-9-oxa-3,7-diazabicyclo[3.3.1]non-3-yl]ethyl}methanesulfonamideYield 62.7%

Conditions

Temperature
160 °C

Procedure

N-[2-(4-Cyanophenoxy)ethyl]-N-[2-(9-oxa-3,7-diazabicyclo[3.3.1]non-3-yl)ethyl]methanesulfonamide (0.079 g, 0.2 mmol; see step (ii) above) and 1-bromomethyl-4-fluorobenzene (0.040 g, 0.21 mmol) and K2CO3 (0.041 g, 0.3 mmol) were was mixed in a microwave vessel and then heated in the microwave reactor for 15 min at 160° C. The mixture was filtered and put on a SCX-II plug. The plug was washed with DCM, acetonitrile, DCM/MeOH (80:20), after which the product was eluted with DCM:MeOH(NH3-satd.), 80:20. The product was purified on a 9 g Horizon prep. chromatography column (A:DCM(1% MeOH), B:DCM/MeOH(NH3-satd.), 80:20. Gradient 0-25% B, 270 mL (9 mL fractions)), which gave 63 mg (62.7%) of the title compound.

Workup

  1. filtrationThe mixture was filtered
  2. washThe plug was washed with DCM, acetonitrile, DCM/MeOH (80:20)
  3. washafter which the product was eluted with DCM
  4. customThe product was purified on a 9 g Horizon prep

Sources & evidence

ORD record
ord-07694a439312435eb29a23129b53abc6
Source dataset
uspto-grants-2008_04
Patent number
US07354917B2

Reaction notes

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