Dimethylacetamide → HCID 178525495, compound

HRID 402651Notes

Reaction equation

HRID 402651 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][C:20]([F:23])=[CH:19][CH:18]=3)=[C:13]([C:24]([O:26][CH3:27])=[O:25])[C:12]2=[O:28])=[CH:2]1.CN(C)[C:31](=[O:33])[CH3:32]>C(O)CCO.O.[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:18]=[CH:19][C:20]([F:23])=[CH:21][CH:22]=3)=[C:13]([C:24]([O:26][CH2:27][CH2:32][CH2:31][OH:33])=[O:25])[C:12]2=[O:28])=[CH:2]1

Participants

6

Reactant 2

HCID 31374DimethylacetamideHCID 178498741HCID 178498741, compound

Product 1

HCID 178525495HCID 178525495, compoundYield 16%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 962WaterSolventHCID 104421,3-PropanediolSolvent

Procedure

A solution of the compound of Example 51 and zinc cluster catalyst (Zn4(OCOCF3)6O) (0.0019 g, 0.0020 mmol) in 1,3-propanediol (0.5 mL) and N,N-dimethylacetamide (0.5 mL) was stirred at 120° C. for 2 h then at 100° C. for 12 h. Cooled to ambient temperature, the reaction mixture was diluted with water, and the precipitate was collected by filtration. Ethyl acetate was added to the filtrate, and the precipitate was collected by filtration. Those precipitates were combined then purified by preparative HPLC to afford the titled compound as solid (0.0067 g, y. 16%).

Workup

  1. filtrationthe precipitate was collected by filtration
  2. additionEthyl acetate was added to the filtrate
  3. filtrationthe precipitate was collected by filtration
  4. customThose precipitates were combined then purified by preparative HPLC

Sources & evidence

ORD record
ord-4a7bfe0013ba4480904e855578a97f96
Source dataset
uspto-grants-2014_06
Patent number
US08742113B2

Reaction notes

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