Ethylene Glycol → HCID 178525605, compound

HRID 402698Notes

Reaction equation

HRID 402698 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][CH:20]=[CH:19][C:18]=3[Cl:23])=[C:13]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:12]2=[O:29])=[CH:2]1.C(O)C[OH:32]>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:22]=[CH:21][CH:20]=[CH:19][C:18]=3[Cl:23])=[C:13]([C:24]([O:26][CH2:27][CH2:28][OH:32])=[O:25])[C:12]2=[O:29])=[CH:2]1

Participants

5

Reactant 2

HCID 174Ethylene GlycolHCID 178469511HCID 178469511, compound

Product 1

HCID 178525605HCID 178525605, compoundYield 29.4%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 31374DimethylacetamideSolvent

Procedure

A solution of the compound (0.10 g, 0.24 mmol) of Example 15, ethylene glycol (0.14 mL, 2.5 mmol) and zinc cluster catalyst (Zn4(OCOCF3)6O) (0.012 g, 0.012 mmol) in N,N-dimethylacetamide (2.0 mL) was stirred with the microwave synthesizer (Biotage Initiator™) at 130° C. for 1 h. Cooled to ambient temperature, the reaction mixture was purified by preparative HPLC to afford the titled compound as solid (0.030 g, y. 29%).

Workup

  1. customthe reaction mixture was purified by preparative HPLC

Sources & evidence

ORD record
ord-14ad2f237d414358afba2ff48b2e9ea2
Source dataset
uspto-grants-2014_06
Patent number
US08742113B2

Reaction notes

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