Methyl Isocyanate → [2-[2-(3-Chlorophenyl)ethynyl]-4-oxa-3,8-diazaspiro[4.5]dec-2-en-8-yl]-(2-furyl)methanone

HRID 2040907Notes

Reaction equation

HRID 2040907 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)=O)[CH2:15]3)[O:12][N:11]=2)[CH:5]=[CH:6][CH:7]=1.ClC1C=C(C#CC2CC3(CCNC3)ON=2)C=CC=1.[O:40]1[CH:44]=[CH:43][CH:42]=[C:41]1[C:45](Cl)=[O:46].CN=C=O>>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]#[C:9][C:10]2[CH2:14][C:13]3([CH2:15][CH2:19][N:16]([C:45]([C:41]4[O:40][CH:44]=[CH:43][CH:42]=4)=[O:46])[CH2:17][CH2:18]3)[O:12][N:11]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 4

HCID 12228Methyl IsocyanateHCID 682422-Furancarbonyl chlorideHCID 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 57493793[2-[2-(3-Chlorophenyl)ethynyl]-4-oxa-3,8-diazaspiro[4.5]dec-2-en-8-yl]-(2-furyl)methanone

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 2-furoyl chloride 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 95:5 to 8:2) giving 105 mg of the title compound. Yield: 60.2%.

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 95:5 to 8:2)

Sources & evidence

ORD record
ord-ec249ce34d3444d68cd43b6b67052e08
Source dataset
uspto-grants-2013_11
Patent number
US08580962B2

Reaction notes

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