3-(3-{4-[(6-Bromohexyl)oxy]but-1-ynyl}phenyl)imidazolidine-2,4-dione → Ammonia

HRID 857106ノート

反応式

HRID 857106 の反応式
BrCCCCCCOCCC#CC1C=C([N:19]2C(=O)CNC2=O)C=CC=1.I[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][O:33][CH2:34][CH2:35][C:36]#[C:37][C:38]1[CH:39]=[C:40]([N:44]2[C:48](=[O:49])[CH2:47][NH:46][C:45]2=[O:50])[CH:41]=[CH:42][CH:43]=1.[NH2:51][CH2:52][C@@H:53]([C:55]1[CH:66]=[CH:65][C:58]2[O:59][C:60]([CH3:64])([CH3:63])[O:61][CH2:62][C:57]=2[CH:56]=1)[OH:54]>CN(C=O)C>[NH3:19].[CH3:63][C:60]1([CH3:64])[O:59][C:58]2[CH:65]=[CH:66][C:55]([C@@H:53]([OH:54])[CH2:52][NH:51][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][O:33][CH2:34][CH2:35][C:36]#[C:37][C:38]3[CH:39]=[C:40]([N:44]4[C:48](=[O:49])[CH2:47][NH:46][C:45]4=[O:50])[CH:41]=[CH:42][CH:43]=3)=[CH:56][C:57]=2[CH2:62][O:61]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 56600231(1R)-2-Amino-1-(2,2-dimethyl-4H-1,3-benzodioxin-6-YL)ethanol

生成物 2

HCID 222AmmoniaHCID 693448833-(3-{4-[(6-{[(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 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
20 °C

実験手順

A mixture 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 (760 mg, 22:3), (1R)-2-amino-1-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)ethanol (800 mg) in DMF (5 ml) was stirred at 20° C. for 22 h. The solvent was removed under reduced pressure and the residue was diluted with EtOAc and washed with water, brine and dried (MgSO4). The solution was concentrated and purified by chromatography on Biotage (40 g) eluting with dichloromethane:MeOH:1M ammonia in methanol (98:1:1 to 95:4:1) to give the title compound (368 mg) LCMS RT=2.59 min.

後処理

  1. customThe solvent was removed under reduced pressure
  2. additionthe residue was diluted with EtOAc
  3. washwashed with water, brine
  4. dry with materialdried (MgSO4)
  5. concentrationThe solution was concentrated
  6. custompurified by chromatography on Biotage (40 g)
  7. washeluting with dichloromethane

出典と根拠

ORDレコード
ord-ce390b7fc52c4b559a61252127f33ef6
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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