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 857111ノート

反応式

HRID 857111 の反応式
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

参加物

6

反応物 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

生成物 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

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 81531Diisopropylethylamine溶媒

反応条件

温度
50 °C

実験手順

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

後処理

  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)

出典と根拠

ORDレコード
ord-3db9163519014a07af2fbcc4bc48845f
出典データセット
uspto-grants-2006_12
特許番号
US07144908B2

反応ノート

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