Diethyl Ether → HCID 178525515, compound

HRID 1500495Notes

Reaction equation

HRID 1500495 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH2:9][NH:10][C:11]([C:13]1[C:14]([OH:31])=[N:15][C:16]([NH:19][C:20](=[O:30])[CH2:21][CH2:22][C:23]([O:25]C(C)(C)C)=[O:24])=[N:17][CH:18]=1)=[O:12].CCOCC>FC(F)(F)C(O)=O>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH2:9][NH:10][C:11]([C:13]1[C:14]([OH:31])=[N:15][C:16]([NH:19][C:20](=[O:30])[CH2:21][CH2:22][C:23]([OH:25])=[O:24])=[N:17][CH:18]=1)=[O:12]

Participants

4

Reactant 2

HCID 3283Diethyl EtherHCID 178451066HCID 178451066, compound

Product 1

HCID 178525515HCID 178525515, compoundYield 38.5%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of tert-butyl 4-({5-[(2,4-dichlorophenyl)methylcarbamoyl]-4-hydroxypyrimidin-2-yl}amino)-4-oxobutanoate (425 mg) in trifluoroacetic acid (3 mL) was left standing at room temperature for 30 minutes. Ether (60 mL) was added to the reaction solution, and the resulting suspension was filtered. The product collected by filtration was washed with ether, dried under reduced pressure, and then purified by reverse phase high performance liquid chromatography (acetonitrile/water, containing 0.1% formic acid) to obtain the title compound (144 mg).

Workup

  1. filtrationthe resulting suspension was filtered
  2. filtrationThe product collected by filtration
  3. washwas washed with ether
  4. customdried under reduced pressure
  5. custompurified by reverse phase high performance liquid chromatography (acetonitrile/water, containing 0.1% formic acid)

Sources & evidence

ORD record
ord-10c703ce207944c4b93f5900fd501827
Source dataset
uspto-grants-2015_12
Patent number
US09206168B2

Reaction notes

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