4-Methyl-1-piperazinecarbonyl chloride → 7-[2-(3-Chlorophenyl)ethynyl]-N-methoxy-N-methyl-9-oxa-3,8-diazaspiro[4.4]non-7-ene-3-carboxamide

HRID 2040903Notes

Reaction equation

HRID 2040903 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]CN(C)CC4)=[O:20])[CH2:15]3)[O:12][N:11]=2)[CH:5]=[CH:6][CH:7]=1.CN1CCN([C:35](Cl)=[O:36])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]([O:36][CH3:35])[CH3:26])=[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 574937997-[2-(3-Chlorophenyl)ethynyl]-N-methoxy-N-methyl-9-oxa-3,8-diazaspiro[4.4]non-7-ene-3-carboxamideYield 54.1%

Procedure

The title compound was synthesized using the method described for the compound of Example 104, replacing N-methoxy-N-methylcarbamoyl chloride for 4-methyl-1-piperazinecarbonyl chloride. After evaporation, the crude was purified by means of automated flash chromatography (SP01®TM-Biotage; gradient petroleum ether-EtOAc 8:2 to 4:6) to afford a pale yellow solid. Yield: 54.1%.

Workup

  1. customAfter evaporation
  2. customthe crude was purified by means of automated flash chromatography (SP01®TM-Biotage; gradient petroleum ether-EtOAc 8:2 to 4:6)
  3. customto afford a pale yellow solid

Sources & evidence

ORD record
ord-dc4d44b787724972919d04150189a013
Source dataset
uspto-grants-2013_11
Patent number
US08580962B2

Reaction notes

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