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Water → N-[2-({(2S)-3-[4-(5-Fluoro-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)-1-piperidinyl]-2-hydroxypropyl}oxy)-4-hydroxyphenyl]acetamide

HRID 132597
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인쇄 미리보기

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HRID 132597 반응식
[F:1][C:2]1[CH:34]=[CH:33][C:5]2[N:6]([CH:10]3[CH2:15][CH2:14][N:13]([CH2:16][C@H:17]([OH:32])[CH2:18][O:19][C:20]4[CH:25]=[C:24]([O:26]C)[CH:23]=[CH:22][C:21]=4[NH:28][C:29](=[O:31])[CH3:30])[CH2:12][CH2:11]3)[C:7](=[O:9])[NH:8][C:4]=2[CH:3]=1.B(Br)(Br)Br.O>ClCCl>[F:1][C:2]1[CH:34]=[CH:33][C:5]2[N:6]([CH:10]3[CH2:15][CH2:14][N:13]([CH2:16][C@H:17]([OH:32])[CH2:18][O:19][C:20]4[CH:25]=[C:24]([OH:26])[CH:23]=[CH:22][C:21]=4[NH:28][C:29](=[O:31])[CH3:30])[CH2:12][CH2:11]3)[C:7](=[O:9])[NH:8][C:4]=2[CH:3]=1
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참가 물질

5

반응물 3

HCID 962WaterHCID 25134Boron tribromideHCID 69199245N-[2-({(2S)-3-[4-(5-fluoro-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)-1-piperidinyl]-2-hydroxypropyl}oxy)-4-methoxyphenyl]acetamide

생성물 1

HCID 69199624N-[2-({(2S)-3-[4-(5-Fluoro-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)-1-piperidinyl]-2-hydroxypropyl}oxy)-4-hydroxyphenyl]acetamide수율 49%

시약·촉매·용매 1

HCID 6344
Dichloromethane
용매
2회

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온도
21 °C

실험 절차

N-[2-({(2S)-3-[4-(5-Fluoro-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)-1-piperidinyl]-2-hydroxypropyl}oxy)-4-methoxyphenyl]acetamide, obtained in Example 32iii), (300 mg, 0.6 mmol) was dissolved in dichloromethane (5 ml) and stirred under nitrogen (N2) at ambient (20-22° C.) temperature. Boron tribromide solution (1 M in dichloromethane, 2 ml, 2 mmol) was added dropwise. After stirring at ambient temperature for 17 hr dichloromethane (5 ml) and water (5 ml) were added. After 1 hr the solvent was removed in vacuo. The residue was purified by gradient flash chromatography on silica gel (CH2Cl2/MeOH, 100/0 to 70/30) and lyophilized yielding the title compound as a white solid (134 mg, 49%).

후처리

  1. additionwere added
  2. customAfter 1 hr the solvent was removed in vacuo
  3. customThe residue was purified by gradient flash chromatography on silica gel (CH2Cl2/MeOH, 100/0 to 70/30)

출처 및 근거

ORD 기록
ord-a6acdedec0554f6d913df7b885b509e2
출처 데이터셋
uspto-grants-2008_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07388020B2

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