2-(Dimethylamino)ethanol → HCID 178476641, compound

HRID 402702Notes

Reaction equation

HRID 402702 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]CC)=[O:25])[C:12]2=[O:29])=[CH:2]1.[CH3:30][N:31]([CH3:35])[CH2:32][CH2:33][OH:34]>CN(C)C1C=CN=CC=1.CN(C)C(=O)C.[Zn]>[C:24]([OH:26])(=[O:25])[CH3:13].[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:34][CH2:33][CH2:32][N:31]([CH3:35])[CH3:30])=[O:25])[C:12]2=[O:29])=[CH:2]1

Participants

6

Reactant 2

HCID 79022-(Dimethylamino)ethanolHCID 178469511HCID 178469511, compound

Product 1

HCID 178476641HCID 178476641, compoundYield 19.5%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 23994ZincCatalystHCID 31374DimethylacetamideSolvent

Procedure

A solution of the compound (0.10 g, 0.24 mmol) of Example 15, 2-(dimethylamino)ethanol (0.40 mL, 4.0 mmol), 4-dimethylaminopyridine (0.010 g, 0.082 mmol) and zinc cluster catalyst (Zn4(OCOCF3)6O) (0.018 g, 0.019 mmol) in N,N-dimethylacetamide (2.0 mL) was stirred at 130° C. for 24 h. Cooled to ambient temperature, the precipitate was removed by filtration. The filtrate was purified by preparative HPLC (aqueous ammonium acetate/acetonitrile as eluents) to afford the titled compound as solid (0.012 g, y. 11%).

Workup

  1. customthe precipitate was removed by filtration
  2. customThe filtrate was purified by preparative HPLC (aqueous ammonium acetate/acetonitrile as eluents)

Sources & evidence

ORD record
ord-a269bc0e0fdd4ebaa726c982c7e07eb0
Source dataset
uspto-grants-2014_06
Patent number
US08742113B2

Reaction notes

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