HCID 69099787, compound → HCID 69099353, compound

HRID 2251479Notes

Reaction equation

HRID 2251479 reaction equation
Br[C:2]1[CH:16]=[C:15]([CH2:17][CH2:18][N:19]([C:31]2[N:36]=[CH:35][C:34]([CH2:37][CH3:38])=[CH:33][N:32]=2)[CH2:20][C:21]2[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][CH:22]=2)[CH:14]=[CH:13][C:3]=1[O:4][C:5]([CH3:12])([CH3:11])[C:6]([O:8][CH2:9][CH3:10])=[O:7].[C:39]([Cu])#[N:40]>CN(C=O)C>[C:39]([C:2]1[CH:16]=[C:15]([CH2:17][CH2:18][N:19]([C:31]2[N:32]=[CH:33][C:34]([CH2:37][CH3:38])=[CH:35][N:36]=2)[CH2:20][C:21]2[CH:22]=[CH:23][C:24]([C:27]([F:29])([F:28])[F:30])=[CH:25][CH:26]=2)[CH:14]=[CH:13][C:3]=1[O:4][C:5]([CH3:12])([CH3:11])[C:6]([O:8][CH2:9][CH3:10])=[O:7])#[N:40]

Participants

4

Reactant 2

HCID 69099787HCID 69099787, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 69099353HCID 69099353, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of ethyl 2-[2-bromo-4-(2-{(5-ethylpyrimidin-2-yl)[4-(trifluoromethyl)benzyl]amino}ethyl)phenoxy]-2-methylpropanoate (from step 1 in the previous example) (188 mg; 0.32 mmol) in DMF (2 ml) was treated with CuCN (37 mg; 0.41 mmol) and heated to reflux overnight under a nitrogen atmosphere. Upon cooling, the reaction mixture was filtered through a plug of silica gel and eluted with DMF. The filtrate was concentrated and partitioned between dichloromethane and brine. The organic phase was dried over MgSO4, filtered and concentrated to afford ethyl 2-[2-cyano-4-(2-{(5-ethylpyrimidin-2-yl)[4-(trifluoromethyl)benzyl]amino}ethyl)phenoxy]-2-methylpropanoate (153 mg), which was used in the next step without further purification.

Workup

  1. temperatureheated
  2. temperatureto reflux overnight under a nitrogen atmosphere
  3. temperatureUpon cooling
  4. filtrationthe reaction mixture was filtered through a plug of silica gel
  5. washeluted with DMF
  6. concentrationThe filtrate was concentrated
  7. custompartitioned between dichloromethane and brine
  8. dry with materialThe organic phase was dried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-c31aeb611b244dfbaf95b9eda038854d
Source dataset
uspto-grants-2008_01
Patent number
US07319104B2

Reaction notes

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