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

HRID 899157Notes

Reaction equation

HRID 899157 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].Br[CH2:29][C:30]1[CH:37]=[CH:36][C:33]([C:34]#[N:35])=[CH:32][CH:31]=1>O>[C:34]([C:33]1[CH:36]=[CH:37][C:30]([CH2:29][N:21]([CH2:20][CH2:19][N:14]2[CH2:15][CH:16]3[O:18][CH:12]([CH2:11][N:10]([CH2:9][C:8]4[CH:7]=[CH:6][C:5]([C:3]#[N:4])=[CH:27][CH:26]=4)[CH2:17]3)[CH2:13]2)[S:22]([CH3:25])(=[O:24])=[O:23])=[CH:31][CH:32]=1)#[N:35]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 869964-(Bromomethyl)benzonitrileHCID 69067702N-{2-[7-(4-Cyano-benzyl)-9-oxa-3,7-diaza-bicyclo[3.3.1]non-3-yl]-ethyl}-methanesulfonamide

Product 1

HCID 11605394N-(4-Cyano-benzyl)-N-{2-[7-(4-cyano-benzyl)-9-oxa-3,7-diaza-bicyclo[3.3.1]non-3-yl]-ethyl}-methanesulfonamideYield 54.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a suspension of sodium hydride (0.013 g of a 60% suspension in mineral oil, washed with pentane) in anhydrous N,N-dimethylformamide (4 mL) was added N-{2-[7-(4-Cyano-benzyl)-9-oxa-3,7-diaza-bicyclo[3.3.1]non-3-yl]-ethyl}-methanesulfonamide (0.109 g, 0.30 mmol) at 0° C. The mixture was stirred for 2 hours while the temperature was allowed to warm to room temperature. At 0° C., 4-bromomethyl-benzonitrile (0.065 g, 0.33 mmol) was added. The mixture was stirred for 2 hours at room temperature, whereupon water (5 mL) was added. The aqueous layer was extracted with dichloromethane (3×5 mL) and the combined organic layers were dried over Na2SO4 and concentrated in vacuo. The crude product was purified by chromatography on silica gel using methanol saturated with ammonia dichloromethane as eluent, which afforded 79 mg (54.9%) of the title compound.

Workup

  1. washwashed with pentane) in anhydrous N,N-dimethylformamide (4 mL)
  2. additionwas added
  3. extractionThe aqueous layer was extracted with dichloromethane (3×5 mL)
  4. dry with materialthe combined organic layers were dried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-3c173ddaa55e4a1284bc072f1709cca2
Source dataset
uspto-grants-2008_04
Patent number
US07354917B2

Reaction notes

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