Benzyl Bromide → N-Benzyl-N-{2-[7-(4-cyanobenzyl)-9-oxa-3,7-diazabicyclo[3.3.1]non-3-yl]-ethyl}methanesulfonamide

HRID 899153Notes

Reaction equation

HRID 899153 reaction equation
[H-].[Na+].[C:3]([C:5]1[CH:27]=[CH:26][C:8]([CH2:9][N:10]2[CH2:17][CH:16]3[O:18][CH:12]([CH2:13][N:14]([CH2:19][CH2:20][NH:21][S:22]([CH3:25])(=[O:24])=[O:23])[CH2:15]3)[CH2:11]2)=[CH:7][CH:6]=1)#[N:4].[CH2:28](Br)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>CN(C=O)C>[CH2:28]([N:21]([CH2:20][CH2:19][N:14]1[CH2:15][CH:16]2[O:18][CH:12]([CH2:11][N:10]([CH2:9][C:8]3[CH:7]=[CH:6][C:5]([C:3]#[N:4])=[CH:27][CH:26]=3)[CH2:17]2)[CH2:13]1)[S:22]([CH3:25])(=[O:24])=[O:23])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 69067702N-{2-[7-(4-Cyano-benzyl)-9-oxa-3,7-diaza-bicyclo[3.3.1]non-3-yl]-ethyl}-methanesulfonamide

Product 1

HCID 11676848N-Benzyl-N-{2-[7-(4-cyanobenzyl)-9-oxa-3,7-diazabicyclo[3.3.1]non-3-yl]-ethyl}methanesulfonamideYield 42.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of NaH (60% in oil, 0.039 g, 1.64 mmol) in dry DMF (10 mL) was added N-{2-[7-(4-cyanobenzyl)-9-oxa-3,7-diazabicyclo[3.3.1]-non-3-yl]ethyl}methanesulfonamide (0.3 g, 0.82 mmol; see Preparation M above) at 0° C. The reaction mixture was stirred for 1 h at room temperature. Benzyl bromide (0.155 g, 0.9 mmol) was added at 0° C. and the reaction mixture stirred at rt for 2 h. The reaction quenched with water, extracted with dichloromethane, washed with water, brine and then dried over sodium sulfate. Solvent evaporation under reduced pressure, followed by column chromatography of the residue over silica gel (using 5% methanol in chloroform as eluent) gave 160 mg of the title compound as a pale yellow solid.

Workup

  1. stirringthe reaction mixture stirred at rt for 2 h
  2. customThe reaction quenched with water
  3. extractionextracted with dichloromethane
  4. washwashed with water, brine
  5. dry with materialdried over sodium sulfate
  6. customSolvent evaporation under reduced pressure

Sources & evidence

ORD record
ord-1cded3cc12a7447aba703097fd572790
Source dataset
uspto-grants-2008_04
Patent number
US07354917B2

Reaction notes

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