4-Methyl-1-piperazinecarbonyl chloride → {3-[(3-Chlorophenyl)ethynyl]-1-oxa-2,7-diazaspiro[4.4]non-2-en-7-yl}(4-methyl piperazin-1-yl)methanone

HRID 2040900Notes

Reaction equation

HRID 2040900 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][NH:16][CH2:15]3)[O:12][N:11]=2)[CH:5]=[CH:6][CH:7]=1.[CH3:19][N:20]1[CH2:25][CH2:24][N:23]([C:26](Cl)=[O:27])[CH2:22][CH2:21]1>ClCCl>[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:26]([N:23]4[CH2:24][CH2:25][N:20]([CH3:19])[CH2:21][CH2:22]4)=[O:27])[CH2:15]3)[O:12][N:11]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 30169354-Methyl-1-piperazinecarbonyl chlorideHCID 574938223-[(3-Chlorophenyl)ethynyl]-1-oxa-2,7-diazaspiro[4.4]non-2-ene

Product 1

HCID 56644861{3-[(3-Chlorophenyl)ethynyl]-1-oxa-2,7-diazaspiro[4.4]non-2-en-7-yl}(4-methyl piperazin-1-yl)methanoneYield 49%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of Compound 27d (150 mg, 0.58 mmol) in dichloromethane (10 mL) was added TEA (0.248 mL, 1.73 mmol) followed by 4-methyl-1-piperazinecarbonyl chloride (122 mg, 0.748 mmol). The reaction mixture was kept under stirring for 20 h. After evaporation the residue was purified by means of automated isocratic RP chromatography (SP01®TM-Biotage; NH4HCO3/AcCN 55:45) affording 91 mg of the title compound as a gummy oil. Yield: 49%.

Workup

  1. customAfter evaporation the residue
  2. customwas purified by means of automated isocratic RP chromatography (SP01®TM-Biotage; NH4HCO3/AcCN 55:45)

Sources & evidence

ORD record
ord-e143fca2fafa4f9a8ea33f921c5dcd7c
Source dataset
uspto-grants-2013_11
Patent number
US08580962B2

Reaction notes

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