Dimethylcarbamoyl Chloride → 3-[(3-Chlorophenyl)ethynyl]-N,N-dimethyl-1-oxa-2,7-diazaspiro[4.4]non-2-ene-7-carboxamide

HRID 2040892Notes

Reaction equation

HRID 2040892 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]([CH3:24])[C:21](Cl)=[O:22]>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:21]([N:20]([CH3:24])[CH3:19])=[O:22])[CH2:15]3)[O:12][N:11]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6598Dimethylcarbamoyl ChlorideHCID 574938223-[(3-Chlorophenyl)ethynyl]-1-oxa-2,7-diazaspiro[4.4]non-2-ene

Product 1

HCID 566446453-[(3-Chlorophenyl)ethynyl]-N,N-dimethyl-1-oxa-2,7-diazaspiro[4.4]non-2-ene-7-carboxamideYield 68.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of Compound 27d (0.12 g, 0.46 mmol) in 10 mL of dichloromethane was added TEA (0.02 mL, 1.38 mmol) followed by N,N-dimethylchloroformamide (0.051 mL, 0.59 mmol). The reaction mixture was stirred at r.t. for 4 h. Afterwards, it was evaporated to dryness and purified by means of automated flash chromatography (SP01®TM-Biotage; gradient Petroleum Ether-EtOAc from 3:7 to 0:1) to give the title compound as a pale yellow solid. Yield: 68.8%.

Workup

  1. customAfterwards, it was evaporated to dryness
  2. custompurified by means of automated flash chromatography (SP01®TM-Biotage; gradient Petroleum Ether-EtOAc from 3:7 to 0:1)

Sources & evidence

ORD record
ord-3b981a52453b4dffbfb1d90d73292174
Source dataset
uspto-grants-2013_11
Patent number
US08580962B2

Reaction notes

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