2-(Dimethylamino)ethanol → HCID 178483906, compound

HRID 402695Notes

Reaction equation

HRID 402695 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][N:31](C)[CH2:32]CO>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][N:31]([CH3:32])[CH3:30])=[O:25])[C:12]2=[O:29])=[CH:2]1

Participants

6

Reactant 2

HCID 79022-(Dimethylamino)ethanolHCID 178469758HCID 178469758, compound

Product 1

HCID 178483906HCID 178483906, compoundYield 2%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 23994ZincCatalystHCID 31374DimethylacetamideSolvent

Procedure

A solution of the compound (0.10 g, 0.25 mmol) of Example 108, 2-(dimethylamino)ethanol (0.40 mL, 4.0 mmol), 4-dimethylaminopyridine (0.0060 g, 0.049 mmol) and zinc cluster catalyst (Zn4(OCOCF3)6O) (0.012 g, 0.012 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 reaction mixture was purified by preparative HPLC to afford the titled compound as solid (0.0023 g, y. 2%).

Workup

  1. customthe reaction mixture was purified by preparative HPLC

Sources & evidence

ORD record
ord-ad59f32adb4c4bf2a8859dff60d15ba3
Source dataset
uspto-grants-2014_06
Patent number
US08742113B2

Reaction notes

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