Ammonium Chloride → 2-[4-Chloro-2-(2H-tetrazol-5-ylmethoxy)-phenoxy]-1-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-ethanone

HRID 11703노트

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HRID 11703 반응식
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:12][CH2:13][C:14]([N:16]2[CH2:21][C@H:20]([CH3:22])[N:19]([CH2:23][C:24]3[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=3)[CH2:18][C@H:17]2[CH3:31])=[O:15])=[C:6]([CH:11]=1)[O:7][CH2:8][C:9]#[N:10].[Cl-].[NH4+].[N-:34]=[N+:35]=[N-:36].[Na+]>CN(C)C=O.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:12][CH2:13][C:14]([N:16]2[CH2:21][C@H:20]([CH3:22])[N:19]([CH2:23][C:24]3[CH:25]=[CH:26][C:27]([F:30])=[CH:28][CH:29]=3)[CH2:18][C@H:17]2[CH3:31])=[O:15])=[C:6]([O:7][CH2:8][C:9]2[N:34]=[N:35][NH:36][N:10]=2)[CH:11]=1

참가 물질

6

반응물 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 69655684(5-Chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-phenoxy)-acetonitrile

생성물 1

HCID 696557872-[4-Chloro-2-(2H-tetrazol-5-ylmethoxy)-phenoxy]-1-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-ethanone수율 14.7%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

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온도
100 °C

실험 절차

To a solution of (5-chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-phenoxy)-acetonitrile (0.11 g, 0.25 mmol) in dimethylformamide (0.50 mL) was added ammonium chloride (0.058 g, 1.1 mmol) and sodium azide (0.055 g, 0.85 mmol). The resulting mixture was stirred at 100° C. for 12 hours. The reaction was cooled and diluted with ethyl acetate and washed with water. The organic layer was washed with saturated aqueous sodium chloride, dried over magnesium sulfate and concentrated in vacuo. Trituration with diethyl ether and methylene chloride gave the title compound (0.018 g, LRMS 489.4, 491.5).

후처리

  1. temperatureThe reaction was cooled
  2. washwashed with water
  3. washThe organic layer was washed with saturated aqueous sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-36ccd70cff014f65bef427d1b3079cf2
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07098212B2

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