HCID 118092832, compound → Ethyl 3-[5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)pyridin-2-yl]propanoate

HRID 2207421Notes

Reaction equation

HRID 2207421 reaction equation
[CH2:1]([O:3][C:4](=[O:31])[CH:5]=[CH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[C:17]([NH:19][C:20]3[N:25]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:23]=[CH:22][N:21]=3)[CH:16]=[C:15]([CH3:30])[CH:14]=2)=[CH:9][N:8]=1)[CH3:2]>CO.C1COCC1.C(O)(C(F)(F)F)=O.[Pd]>[CH3:30][C:15]1[CH:14]=[C:13]([C:10]2[CH:11]=[CH:12][C:7]([CH2:6][CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:31])=[N:8][CH:9]=2)[CH:18]=[C:17]([NH:19][C:20]2[N:25]=[C:24]([C:26]([F:29])([F:27])[F:28])[CH:23]=[CH:22][N:21]=2)[CH:16]=1

Participants

6

Reactant 1

HCID 118092832HCID 118092832, compound

Product 1

HCID 131735915Ethyl 3-[5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)pyridin-2-yl]propanoate

Reagents, catalysts & solvents 4

HCID 6422Trifluoroacetic acidCatalystHCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Pd/C (10.0 mg, 9.40 mol) was added to a solution of ethyl-3-[5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)pyridin-2-yl]prop-2-enoate (96.0 mg, 0.224 mmol) in MeOH (2.00 mL) and THF (1.00 mL). One drop of TFA was added to the reaction mixture and was purged and flushed with argon (3×). The reaction mixture was stirred for 4 hours at room temperature under an atmosphere of hydrogen. The mixture was filtered through CELITE and concentrated under reduced pressure. The residue was purified by silica gel chromatography (3:7 ethyl acetate in hexanes) to afford ethyl 3-[5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)pyridin-2-yl]propanoate. C22H22F3N4O2 [M+H]431. found 431.

Workup

  1. customwas purged
  2. customflushed with argon (3×)
  3. filtrationThe mixture was filtered through CELITE
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel chromatography (3:7 ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-521850419ec04d10ad54404d3e7f1da2
Source dataset
uspto-grants-2016_06
Patent number
US09376418B2

Reaction notes

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