2-Methoxyethanol → HCID 178496320, compound

HRID 402693Notes

Reaction equation

HRID 402693 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.[CH3:30][O:31]CCO>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][O:31][CH3:30])=[O:25])[C:12]2=[O:29])=[CH:2]1

Participants

6

Reactant 2

HCID 80192-MethoxyethanolHCID 178469758HCID 178469758, compound

Product 1

HCID 178496320HCID 178496320, compoundYield 5.5%

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, 2-methoxyethanol (0.20 mL, 2.6 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 3.5 h. Cooled to ambient temperature, the reaction mixture was purified by preparative HPLC to afford the titled compound as solid (0.0029 g, y. 5%).

Workup

  1. customthe reaction mixture was purified by preparative HPLC

Sources & evidence

ORD record
ord-0d9a2df44477447d916a654616e15b36
Source dataset
uspto-grants-2014_06
Patent number
US08742113B2

Reaction notes

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