3-Bromo-1,1,1-trifluoro-2-propanone → HCID 178453685, compound

HRID 2171515Notes

Reaction equation

HRID 2171515 reaction equation
Br[CH2:2][C:3](=[O:8])[C:4]([F:7])([F:6])[F:5].CC1C=C(C)[N:12]([C:16]([NH:18][C:19]([NH:21][CH2:22][CH2:23][NH:24][C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[S:20])=N)N=1>CS(C)=O>[C:16]([N:18]1[C:3]([OH:8])([C:4]([F:7])([F:6])[F:5])[CH2:2][S:20]/[C:19]/1=[N:21]\[CH2:22][CH2:23][NH:24][C:25](=[O:31])[O:26][C:27]([CH3:29])([CH3:28])[CH3:30])#[N:12]

Participants

4

Reactant 2

HCID 790083-Bromo-1,1,1-trifluoro-2-propanoneHCID 178426534HCID 178426534, compound

Product 1

HCID 178453685HCID 178453685, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 484 mg (2.4 mmol) of 3-bromo-1,1,1-trifluoropropan-2-one in 12 ml of DMSO is added dropwise to the crude mixture from Example 72A while cooling in ice, and the mixture is then heated at 60° C. for 1 h. The crude mixture is poured into ice-water and extracted three times with ethyl acetate. After the combined organic phases have been dried, the solvent is completely removed and the residue is purified by subsequent purification by preparative HPLC. 640 mg (67% of theory) of the product are obtained as a solid.

Workup

  1. temperaturewhile cooling in ice
  2. extractionextracted three times with ethyl acetate
  3. customAfter the combined organic phases have been dried
  4. customthe solvent is completely removed
  5. customthe residue is purified by subsequent purification by preparative HPLC
  6. custom640 mg (67% of theory) of the product are obtained as a solid

Sources & evidence

ORD record
ord-b48a219aeb124ee1bfd59a3c53c5bcea
Source dataset
uspto-grants-2015_06
Patent number
US09051323B2

Reaction notes

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