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

HRID 857106Notes

Reaction equation

HRID 857106 reaction equation
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

Participants

6

Reactant 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

Product 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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
20 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-ce390b7fc52c4b559a61252127f33ef6
Source dataset
uspto-grants-2006_12
Patent number
US07144908B2

Reaction notes

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