Diethylcarbamoyl chloride → 2-[2-(3-Chlorophenyl)ethynyl]-N,N-diethyl-4-oxa-3,8-diazaspiro[4.5]dec-2-ene-8-carboxamide

HRID 2040909Notes

Reaction equation

HRID 2040909 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]#[C:9][C:10]2[CH2:14][C:13]3(CCN(C(N)=O)C3)[O:12][N:11]=2)[CH:5]=[CH:6][CH:7]=1.ClC1C=C(C#CC2C[C:34]3([CH2:39][CH2:38][NH:37][CH2:36]3)ON=2)C=CC=1.[CH2:40]([N:42]([CH2:46][CH3:47])[C:43](Cl)=[O:44])[CH3:41].CN=C=O>>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]#[C:9][C:10]2[CH2:14][C:13]3([CH2:47][CH2:46][N:42]([C:43]([N:37]([CH2:38][CH3:39])[CH2:36][CH3:34])=[O:44])[CH2:40][CH2:41]3)[O:12][N:11]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 4

HCID 6916Diethylcarbamoyl chlorideHCID 12228Methyl IsocyanateHCID 566446463-[(3-Chlorophenyl)ethynyl]-1-oxa-2,7-diazaspiro[4.4]non-2-ene-7-carboxamideHCID 574938223-[(3-Chlorophenyl)ethynyl]-1-oxa-2,7-diazaspiro[4.4]non-2-ene

Product 1

HCID 574937952-[2-(3-Chlorophenyl)ethynyl]-N,N-diethyl-4-oxa-3,8-diazaspiro[4.5]dec-2-ene-8-carboxamide

Procedure

The title compound was synthesized following the method herein described for the compound of Example 96 but replacing Compound 22c for Compound 27d and N,N-diethyl chloroformamide for methylisocyanate. After the usual work-up procedure the crude was purified by means of automated flash chromatography (Isolera®TM-Biotage; gradient Petroleum Ether-EtOAc from 8:2 to 6:4) giving the title compound. Yield: 47.1%.

Workup

  1. customThe title compound was synthesized
  2. customAfter the usual work-up procedure the crude was purified by means of automated flash chromatography (Isolera®TM-Biotage; gradient Petroleum Ether-EtOAc from 8:2 to 6:4)

Sources & evidence

ORD record
ord-3a97f3948db04661b105aa580aa34615
Source dataset
uspto-grants-2013_11
Patent number
US08580962B2

Reaction notes

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