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Dimethylformamide → N-[5-Bromo-2-({(2S)-3-[4-(5-fluoro-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)-1-piperidinyl]-2-hydroxypropyl}oxy)4-methoxyphenyl]acetamide

HRID 132595
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HRID 132595 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][CH3:27])[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.CN(C=O)C.B(Br)(Br)[Br:41]>C(Cl)Cl>[Br:41][C:23]1[C:24]([O:26][CH3:27])=[CH:25][C:20]([O:19][CH2:18][C@@H:17]([OH:32])[CH2:16][N:13]2[CH2:12][CH2:11][CH:10]([N:6]3[C:5]4[CH:33]=[CH:34][C:2]([F:1])=[CH:3][C:4]=4[NH:8][C:7]3=[O:9])[CH2:15][CH2:14]2)=[C:21]([NH:28][C:29](=[O:31])[CH3:30])[CH:22]=1
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참가 물질

5

반응물 3

HCID 6228DimethylformamideHCID 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 69196349N-[5-Bromo-2-({(2S)-3-[4-(5-fluoro-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)-1-piperidinyl]-2-hydroxypropyl}oxy)4-methoxyphenyl]acetamide수율 45%

시약·촉매·용매 1

HCID 6344
Dichloromethane
용매
2회

실험 절차

To a stirred suspension of N-[2-({(2S)-3-[4-(5-fluoro-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)-1-piperidinyl]-2-hydroxypropyl}oxy)-4-methoxyphenyl]acetamide (Example 32 iii)) (0.17 g, 0.36 mmol) in CH2Cl2 (5 ml) with some drops of DMF a solution of boron tribromide (BBr3) in dichloromethane (CH2Cl2) (1M, 1.08 mmol, 1.08 ml) was added dropwise under nitrogen. The stirring was continued overnight art room temperature. Then the reaction mixture was quenched with methanol, diluted with water and extracted with dichloromethane (CH2Cl2) (2×10 ml) and ethyl acetate (2×10 ml). The combined organic extracts were dried with sodium sulphate and concentrated in vacuo. The residue was purified by flash chromatography of silica gel (CH2Cl2/MeOH, 9:1) to give a colourless solid (89 mg, 0.16 mmol, 45%).

후처리

  1. additionwas added dropwise under nitrogen
  2. customart room temperature
  3. customThen the reaction mixture was quenched with methanol
  4. additiondiluted with water
  5. extractionextracted with dichloromethane (CH2Cl2) (2×10 ml) and ethyl acetate (2×10 ml)
  6. dry with materialThe combined organic extracts were dried with sodium sulphate
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash chromatography of silica gel (CH2Cl2/MeOH, 9:1)

출처 및 근거

ORD 기록
ord-33f21adb4f9f4262b77f3582aafceb01
출처 데이터셋
uspto-grants-2008_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07388020B2

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