Ethylene Glycol → HCID 178525606, compound

HRID 402636Notes

Reaction equation

HRID 402636 reaction equation
[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]([CH:10]=[C:11]2[O:15][C:14]([NH:16][C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=3)=[C:13]([C:24]([O:26][CH3:27])=[O:25])[C:12]2=[O:28])=[CH:2]1.C(O)[CH2:30][OH:31]>CN(C)C(=O)C.[Zn]>[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]([CH:10]=[C:11]2[O:15][C:14]([NH:16][C:17]3[CH:18]=[CH:19][C:20]([F:23])=[CH:21][CH:22]=3)=[C:13]([C:24]([O:26][CH2:27][CH2:30][OH:31])=[O:25])[C:12]2=[O:28])=[CH:2]1

Participants

5

Reactant 2

HCID 174Ethylene GlycolHCID 178498741HCID 178498741, compound

Product 1

HCID 178525606HCID 178525606, compoundYield 10%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 31374DimethylacetamideSolvent

Procedure

Under a nitrogen atmosphere, a solution of the compound (0.038 g, 0.10 mmol) of Example 51, ethylene glycol (0.50 mL, 9.0 mmol) and zinc cluster catalyst (Zn4(OCOCF3)6O) (0.0019 g, 0.0020 mmol) in N,N-dimethylacetamide (0.5 mL) was stirred with the microwave synthesizer (Biotage Initiator™) at 150° C. for 1 h. Cooled to ambient temperature, the precipitate was removed by filtration. The filtrate was purified by preparative HPLC to afford the titled compound as solid (0.0040 g, y. 10%).

Workup

  1. customthe precipitate was removed by filtration
  2. customThe filtrate was purified by preparative HPLC

Sources & evidence

ORD record
ord-d155de63ee58422980cf27e770b8034a
Source dataset
uspto-grants-2014_06
Patent number
US08742113B2

Reaction notes

Loading…