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4-Fluorobenzyl bromide → 4-{3-[7-(4-Fluorobenzyl)-9-oxa-3,7-diazabicyclo[3.3.1]non-3-yl]-2-hydroxypropoxy}benzonitrile

HRID 898795
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인쇄 미리보기

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HRID 898795 반응식
[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6]Br)=[CH:4][CH:3]=1.[OH:10][CH:11]([CH2:22][N:23]1[CH2:30][CH:29]2[O:31][CH:25]([CH2:26][NH:27][CH2:28]2)[CH2:24]1)[CH2:12][O:13][C:14]1[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][CH:15]=1>C(Cl)Cl.CC#N>[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][N:27]2[CH2:28][CH:29]3[O:31][CH:25]([CH2:24][N:23]([CH2:22][CH:11]([OH:10])[CH2:12][O:13][C:14]4[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][CH:15]=4)[CH2:30]3)[CH2:26]2)=[CH:4][CH:3]=1
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참가 물질

5

반응물 2

HCID 680214-Fluorobenzyl bromideHCID 185403994-{[2-Hydroxy-3-(9-oxa-3,7-diazabicyclo[3.3.1]non-3-yl)propyl]oxy}benzonitrile

생성물 1

HCID 98017154-{3-[7-(4-Fluorobenzyl)-9-oxa-3,7-diazabicyclo[3.3.1]non-3-yl]-2-hydroxypropoxy}benzonitrile

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 6344Dichloromethane용매

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온도
50 °C

실험 절차

A solution of 4-fluorobenzyl bromide (14.17 mg, 0.075 mmol) in DCM (0.5 mL) of was added, together with TEA (20 mg, 0.2 mmol) to a solution of 4-{[2-hydroxy-3-(9-oxa-3,7-diazabicyclo[3.3.1]non-3-yl)-propyl]oxy}benzonitrile (Preparation K; 15.2 mg, 0.05 mmol) in MeCN (0.5 mL). The mixture was stirred at 50° C. for 4 days before being concentrated in vacuo. The resulting residue was dissolved in CHCl3 and added to a solid-phase extraction plug (CBA, 0.4 g). The plug was washed with CHCl3 (4×0.3 mL), and the product was finally eluted with CHCl3:MeOH:TEA (5×0.3 mL of 8:1:1) to give the title compound.

후처리

  1. concentrationbefore being concentrated in vacuo
  2. dissolutionThe resulting residue was dissolved in CHCl3
  3. additionadded to a solid-phase extraction plug (CBA, 0.4 g)
  4. washThe plug was washed with CHCl3 (4×0.3 mL)
  5. washthe product was finally eluted with CHCl3

출처 및 근거

ORD 기록
ord-0989e849bc084f2b82a6595fb2285921
출처 데이터셋
uspto-grants-2008_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07351821B2

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