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

HRID 857106노트

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HRID 857106 반응식
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

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 56600231(1R)-2-Amino-1-(2,2-dimethyl-4H-1,3-benzodioxin-6-YL)ethanol

생성물 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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
20 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-ce390b7fc52c4b559a61252127f33ef6
출처 데이터셋
uspto-grants-2006_12
특허 번호
US07144908B2

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