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

HRID 2040910Notes

Reaction equation

HRID 2040910 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.[Cl:40][C:41]1[CH:42]=[C:43]([CH:47]=[CH:48][CH:49]=1)[C:44](Cl)=[O:45].CN=C=O>>[Cl:40][C:41]1[CH:42]=[C:43]([C:44]([N:16]2[CH2:19][CH2:15][C:13]3([CH2:14][C:10]([C:9]#[C:8][C:4]4[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=4)=[N:11][O:12]3)[CH2:18][CH2:17]2)=[O:45])[CH:47]=[CH:48][CH:49]=1

Participants

5

Reactant 4

HCID 12228Methyl IsocyanateHCID 69252Benzoyl chloride, 3-chloro-HCID 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 56644862(3-Chlorophenyl)-[2-[2-(3-chlorophenyl)ethynyl]-4-oxa-3,8-diazaspiro[4.5]dec-2-en-8-yl]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 3-chlorobenzoyl chloride for methyl isocyanate. 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 122 mg of the title compound a s a pale yellow oil. Yield: 67.5%.

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-09d2750f4f5e41078bf26fb6f0769cfd
Source dataset
uspto-grants-2013_11
Patent number
US08580962B2

Reaction notes

Loading…