4-Methyl-1-piperazinecarbonyl chloride → [7-[2-(3-Chlorophenyl)ethynyl]-9-oxa-3,8-diazaspiro[4.4]non-7-en-3-yl]-pyrrolidin-1-yl-methanone

HRID 2040902Notes

Reaction equation

HRID 2040902 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(C)[CH2:23][CH2:22]4)=[O:20])[CH2:15]3)[O:12][N:11]=2)[CH:5]=[CH:6][CH:7]=1.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([O:12][N:11]=2)[CH2:18][CH2:17][N:16]([C:19]([N:21]2[CH2:26][CH2:25][CH2:23][CH2:22]2)=[O:20])[CH2:15]3)[CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 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 57493783[7-[2-(3-Chlorophenyl)ethynyl]-9-oxa-3,8-diazaspiro[4.4]non-7-en-3-yl]-pyrrolidin-1-yl-methanoneYield 72.8%

Procedure

The title compound was synthesized using the method described for the compound of Example 104, replacing 1-pyrrolidincarbonyl chloride for 4-methyl-1-piperazinecarbonyl chloride. After the usual work-up procedure, the crude was purified by means of automated flash chromatography (SP01®TM-Biotage; CHCl3-1.4N methanolic ammonia 100:0.5) to afford an ivory solid. Yield: 72.8%.

Workup

  1. customAfter the usual work-up procedure, the crude was purified by means of automated flash chromatography (SP01®TM-Biotage; CHCl3-1.4N methanolic ammonia 100:0.5)
  2. customto afford an ivory solid

Sources & evidence

ORD record
ord-4e319a6d9090495681509550a98f0a33
Source dataset
uspto-grants-2013_11
Patent number
US08580962B2

Reaction notes

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