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 899157노트

반응식

HRID 899157 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].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]

참가 물질

5

반응물 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

생성물 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}-methanesulfonamide수율 54.9%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-3c173ddaa55e4a1284bc072f1709cca2
출처 데이터셋
uspto-grants-2008_04
특허 번호
US07354917B2

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