1,8-Diazabicyclo(5.4.0)undec-7-ene → Capadenoson

HRID 2214971Notes

Reaction equation

HRID 2214971 reaction equation
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][OH:19])=[CH:12][CH:11]=2)[C:5]([C:20]#[N:21])=[C:4]([SH:22])[N:3]=1.N12CCCN=C1CCCCC2.Cl[CH2:35][C:36]1[N:37]=[C:38]([C:41]2[CH:46]=[CH:45][C:44]([Cl:47])=[CH:43][CH:42]=2)[S:39][CH:40]=1>CN(C=O)C>[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[CH:11]=[CH:12][C:13]([O:16][CH2:17][CH2:18][OH:19])=[CH:14][CH:15]=2)[C:5]([C:20]#[N:21])=[C:4]([S:22][CH2:35][C:36]2[N:37]=[C:38]([C:41]3[CH:46]=[CH:45][C:44]([Cl:47])=[CH:43][CH:42]=3)[S:39][CH:40]=2)[N:3]=1

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 6102974-(Chloromethyl)-2-(4-chlorophenyl)-1,3-thiazoleHCID 178510483HCID 178510483, compound

Product 1

HCID 9936489Capadenoson

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6.91 g (22.12 mmol) of 2-amino-4-[4-(2-hydroxyethoxy)phenyl]-6-sulphanyl-pyridine-3,5-dicarbonitrile are dissolved in 150 ml of DMF. 7.44 g (66.35 mmol) of 1,8-diazabicyclo[5.4.0]undec-7-ene and 10.8 g (44.24 mmol) of 4-chloromethyl-2-(4-chlorophenyl)-1,3-thiazole are then added. The suspension is stirred at RT overnight, 50 g of silica gel are added and the mixture is concentrated under reduced pressure. The substance mixture on the silica gel is purified by chromatography on silica gel (mobile phase: toluene to toluene/ethyl acetate, 1:1 mixture). This gives 5.5 g (47% of theory) of product.

Workup

  1. addition50 g of silica gel are added
  2. concentrationthe mixture is concentrated under reduced pressure
  3. customThe substance mixture on the silica gel is purified by chromatography on silica gel (mobile phase: toluene to toluene/ethyl acetate, 1:1 mixture)

Sources & evidence

ORD record
ord-3eedfc77f8ce4e568363670bc9eb68b1
Source dataset
uspto-grants-2006_09
Patent number
US07109218B2

Reaction notes

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