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

HRID 899153노트

반응식

HRID 899153 반응식
[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

참가 물질

5

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-1cded3cc12a7447aba703097fd572790
출처 데이터셋
uspto-grants-2008_04
특허 번호
US07354917B2

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