Ethylene Glycol → HCID 178482909, compound

HRID 402690Notes

Reaction equation

HRID 402690 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]([N:16]([CH3:23])[CH2:17][C:18]3[S:19][CH:20]=[CH:21][CH:22]=3)=[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)C1C=CN=CC=1.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]([N:16]([CH3:23])[CH2:17][C:18]3[S:19][CH:20]=[CH:21][CH:22]=3)=[C:13]([C:24]([O:26][CH2:27][CH2:28][OH:32])=[O:25])[C:12]2=[O:29])=[CH:2]1

Participants

6

Reactant 2

HCID 174Ethylene GlycolHCID 178469758HCID 178469758, compound

Product 1

HCID 178482909HCID 178482909, compoundYield 11.9%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 23994ZincCatalystHCID 31374DimethylacetamideSolvent

Procedure

A solution of the compound (0.050 g, 0.12 mmol) of Example 108, ethylene glycol (0.20 mL, 3.6 mmol), 4-dimethylaminopyridine (0.0030 g, 0.024 mmol) and zinc cluster catalyst (Zn4(OCOCF3)6O) (0.0058 g, 0.0061 mmol) in N,N-dimethylacetamide (0.5 mL) was stirred with the microwave synthesizer (Biotage Initiator™) at 150° C. for 30 min. Cooled to ambient temperature, the precipitate was removed by filtration. The filtrate was purified by preparative HPLC to afford the titled compound as solid (0.0061 g, y. 10%).

Workup

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

Sources & evidence

ORD record
ord-679b121270c843588131f2af0624776b
Source dataset
uspto-grants-2014_06
Patent number
US08742113B2

Reaction notes

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