2-Oxoimidazolidine-1-carbonyl chloride → 1-({3-[(3-Chlorophenyl)ethynyl]-1-oxa-2,7-diazaspiro[4.4]non-2-en-7-yl}carbonyl)imidazolidin-2-one

HRID 2040901Notes

Reaction equation

HRID 2040901 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]#[C:9][C:10]2[CH2:14][C:13]3([CH2:18][CH2:17][N:16]([C:19]([N:21]4[CH2:26][CH2:25][N:24]([CH3:27])CC4)=[O:20])[CH2:15]3)[O:12][N:11]=2)[CH:5]=[CH:6][CH:7]=1.ClC(N1CCNC1=O)=[O:30].CN1CCN(C(Cl)=O)CC1>>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]#[C:9][C:10]2[CH2:14][C:13]3([CH2:18][CH2:17][N:16]([C:19]([N:21]4[CH2:26][CH2:25][NH:24][C:27]4=[O:30])=[O:20])[CH2:15]3)[O:12][N:11]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 832412-Oxoimidazolidine-1-carbonyl chlorideHCID 30169354-Methyl-1-piperazinecarbonyl chlorideHCID 56644861{3-[(3-Chlorophenyl)ethynyl]-1-oxa-2,7-diazaspiro[4.4]non-2-en-7-yl}(4-methyl piperazin-1-yl)methanone

Product 1

HCID 574937821-({3-[(3-Chlorophenyl)ethynyl]-1-oxa-2,7-diazaspiro[4.4]non-2-en-7-yl}carbonyl)imidazolidin-2-oneYield 51.3%

Procedure

The title compound was synthesized using the method described for the compound of Example 104, replacing 1-chlorocarbonyl-2-imidazolidinone for by 4-methyl-1-piperazinecarbonyl chloride. After evaporation, the crude was purified by means of automated flash chromatography (SP01®TM-Biotage; gradient EtOAc-MeOH from 95:5 to 8:2) to afford a yellowish solid. Yield: 51.3%.

Workup

  1. customAfter evaporation
  2. customthe crude was purified by means of automated flash chromatography (SP01®TM-Biotage; gradient EtOAc-MeOH from 95:5 to 8:2)
  3. customto afford a yellowish solid

Sources & evidence

ORD record
ord-bc65024a254c4619b7e89e9c0eb521da
Source dataset
uspto-grants-2013_11
Patent number
US08580962B2

Reaction notes

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