Glycine tert-butyl ester → Tert-butyl 2-(2-cyano-6-(trifluoromethyl)quinolin-4-ylamino)acetate

HRID 1896879Notes

Reaction equation

HRID 1896879 reaction equation
O[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([F:15])([F:14])[F:13])[CH:10]=2)[N:5]=[C:4]([C:16]#[N:17])[CH:3]=1.C1CN([P+](Br)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.[NH2:42][CH2:43][C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45]>O1CCOCC1>[C:16]([C:4]1[CH:3]=[C:2]([NH:42][CH2:43][C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([F:15])([F:14])[F:13])[CH:10]=2)[N:5]=1)#[N:17]

Participants

5

Reactant 3

HCID 151417Glycine tert-butyl esterHCID 2733179PyBroPHCID 1785102352-Quinolinecarbonitrile, 4-hydroxy-6-(trifluoromethyl)-

Product 1

HCID 58562608Tert-butyl 2-(2-cyano-6-(trifluoromethyl)quinolin-4-ylamino)acetate

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 4-hydroxy-6-(trifluoromethyl)quinoline-2-carbonitrile (2 g, 8.4 mmol) from example 21, step D, in dry dioxane was added TEA (2.9 mL, 21 mmol) and PyBroP (4.75 g, 10 mmol) and stirred at 50 C for 2 hour. To this solution tert-butyl 2-aminoacetate (1.3 g, 10.1 mmol) was added and stirred at 30° C. for 24 h. The solution was concentrated in vacuo. Water was added to the residue and extracted with EtOAc. The ethyl acetate was removed under vacuum and the residue was purified by flash chromatography (silica gel, 0 to 80% EtOAc in hexane) to give the title compound.

Workup

  1. stirringstirred at 30° C. for 24 h
  2. concentrationThe solution was concentrated in vacuo
  3. additionWater was added to the residue
  4. extractionextracted with EtOAc
  5. customThe ethyl acetate was removed under vacuum
  6. customthe residue was purified by flash chromatography (silica gel, 0 to 80% EtOAc in hexane)

Sources & evidence

ORD record
ord-5300833c7104425298df5304595366a2
Source dataset
uspto-grants-2013_08
Patent number
US08518969B2

Reaction notes

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