3-(3-{4-[(6-Bromohexyl)oxy]but-1-ynyl}phenyl)imidazolidine-2,4-dione → 3-(3-{4-[(6-{Benzyl[(2R)-2-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-2-hydroxyethyl]amino}hexyl)oxy]but-1-ynyl}phenyl)imidazolidine-2,4-dione

HRID 857111노트

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HRID 857111 반응식
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][C:11]#[C:12][C:13]1[CH:14]=[C:15]([N:19]2[C:23](=[O:24])[CH2:22][NH:21][C:20]2=[O:25])[CH:16]=[CH:17][CH:18]=1.ICCCCCCOCCC#CC1C=C(N2C(=O)CNC2=O)C=CC=1.[CH2:51]([NH:58][CH2:59][C@@H:60]([C:62]1[CH:73]=[CH:72][C:65]2[O:66][C:67]([CH3:71])([CH3:70])[O:68][CH2:69][C:64]=2[CH:63]=1)[OH:61])[C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1>C(#N)C.C(N(C(C)C)CC)(C)C>[CH2:51]([N:58]([CH2:59][C@@H:60]([C:62]1[CH:73]=[CH:72][C:65]2[O:66][C:67]([CH3:70])([CH3:71])[O:68][CH2:69][C:64]=2[CH:63]=1)[OH:61])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][C:11]#[C:12][C:13]1[CH:14]=[C:15]([N:19]2[C:23](=[O:24])[CH2:22][NH:21][C:20]2=[O:25])[CH:16]=[CH:17][CH:18]=1)[C:52]1[CH:53]=[CH:54][CH:55]=[CH:56][CH:57]=1

참가 물질

6

반응물 3

HCID 218670753-(3-{4-[(6-Bromohexyl)oxy]but-1-ynyl}phenyl)imidazolidine-2,4-dioneHCID 218670893-(3-{4-[(6-Iodohexyl)oxy]but-1-ynyl}phenyl)imidazolidine-2,4-dioneHCID 69196697(1R)-2-(benzylamino)-1-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)ethanol

생성물 1

HCID 693447783-(3-{4-[(6-{Benzyl[(2R)-2-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-2-hydroxyethyl]amino}hexyl)oxy]but-1-ynyl}phenyl)imidazolidine-2,4-dione

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 81531Diisopropylethylamine용매

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온도
50 °C

실험 절차

A solution of 3-(3-{4-[(6-bromohexyl)oxy]but-1-ynyl}phenyl)imidazolidine-2,4-dione and 3-(3-{4-[(6-iodohexyl)oxy]but-1-ynyl}phenyl)imidazolidine-2,4-dione (3:1, 23.98 g) in acetonitrile (240 ml) and diisopropylethylamine (20 ml) was treated with (1R)-2-(benzylamino)-1-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)ethanol (18.22 g) and the mixture was heated to 50° C. for 5 days. The solvent was removed under reduced pressure, the residue was diluted with EtOAc (250 ml) and washed with water. The aqueous phase was re-extracted with EtOAc (75 ml) and the combined organic solutions were washed with brine, dried (MgSO4), and evaporated. The residue was purified by chromatography on flash silica gel eluting with dichloromethane-EtOAc (1:1) to give the title compound (17.25 g) LCMS RT=2.80 min

후처리

  1. customThe solvent was removed under reduced pressure
  2. additionthe residue was diluted with EtOAc (250 ml)
  3. washwashed with water
  4. extractionThe aqueous phase was re-extracted with EtOAc (75 ml)
  5. washthe combined organic solutions were washed with brine
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. customThe residue was purified by chromatography on flash silica gel eluting with dichloromethane-EtOAc (1:1)

출처 및 근거

ORD 기록
ord-3db9163519014a07af2fbcc4bc48845f
출처 데이터셋
uspto-grants-2006_12
특허 번호
US07144908B2

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