3-[(3-Chlorophenyl)ethynyl]-N,N-dimethyl-1-oxa-2,7-diazaspiro[4.4]non-2-ene-7-carboxamide → 2-[2-(3-Chlorophenyl)ethynyl]-N,N-dimethyl-4-oxa-3,8-diazaspiro[4.5]dec-2-ene-8-carboxamide

HRID 2040913Notes

Reaction equation

HRID 2040913 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]([CH3:23])[CH3:22])=[O:20])[CH2:15]3)[O:12][N:11]=2)[CH:5]=[CH:6][CH:7]=1.Cl[C:25]1C=C(C#CC2CC3(CCN(C(OC(C)(C)C)=O)C3)ON=2)C=CC=1>>[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]([CH3:22])[CH3:23])=[O:20])[CH2:15][CH2:25]3)[O:12][N:11]=2)[CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 566446453-[(3-Chlorophenyl)ethynyl]-N,N-dimethyl-1-oxa-2,7-diazaspiro[4.4]non-2-ene-7-carboxamideHCID 57493821Tert-butyl 3-[(3-chlorophenyl)ethynyl]-1-oxa-2,7-diazaspiro[4.4]non-2-ene-7-carboxylate

Product 1

HCID 566448652-[2-(3-Chlorophenyl)ethynyl]-N,N-dimethyl-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 95 but replacing Compound 22d for Compound 27c. After the usual work-up procedure the crude was purified by means of automated flash chromatography (Isolera®TM-Biotage; gradient Petroleum Ether-EtOAc from 3:7 to 0:1) giving pale yellow solid of the title compound. Yield: 66.2%.

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 3:7 to 0:1)

Sources & evidence

ORD record
ord-10cf996015d14fa398e38efd4f951484
Source dataset
uspto-grants-2013_11
Patent number
US08580962B2

Reaction notes

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