Trifluoroacetic acid → N-((6-amino-2,4-dimethylpyridin-3-yl)methyl)-3-benzyl-1,2,4-oxadiazole-5-carboxamide

HRID 928365Notes

Reaction equation

HRID 928365 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[C:12]([CH3:14])[C:11]([CH2:15][NH:16][C:17]([C:19]2[O:23][N:22]=[C:21]([CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[N:20]=2)=[O:18])=[C:10]([CH3:31])[N:9]=1)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:7][C:8]1[N:9]=[C:10]([CH3:31])[C:11]([CH2:15][NH:16][C:17]([C:19]2[O:23][N:22]=[C:21]([CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[N:20]=2)=[O:18])=[C:12]([CH3:14])[CH:13]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58081166(5-{[(3-Benzyl-[1,2,4]oxadiazole-5-carbonyl)-amino]-methyl}-4,6-dimethyl-pyridin-2-yl)-carbamic acid tert-butyl ester

Product 1

HCID 58081292N-((6-amino-2,4-dimethylpyridin-3-yl)methyl)-3-benzyl-1,2,4-oxadiazole-5-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of (5-{[(3-Benzyl-[1,2,4]oxadiazole-5-carbonyl)-amino]-methyl}-4,6-dimethyl-pyridin-2-yl)-carbamic acid tert-butyl ester (65 mg, 0.09 mmol), 2 mL TFA and 4 mL DCM was stirred of room temperature for 1 h. The mixture was evaporated in vacuo and the residue was purified by prep HPLC (Macherey-Nagel Nucleosil 250×40 mm, 5 to 100% ACN and 0.1% TFA, flow 40ml/min). Aq. NaHCO3-solution was added to the product containing fractions and after evaporation the aq. layer was extracted with ethyl acetate. The organic layer was dried over MgSO4 and concentrated to give the title compound. 1H-NMR (DMSO-d6, 400 MHz) 9.43 (t, 1H), 7.25-7.36 (m, 5H), 6.10 (s, 1H), 5.70 (s, 2H), 4.35 (d, 2H), 4.18 (s, 2H), 2.29 (s, 3H), 2.16 (s, 3H); LCMS (method A) RtA=1.024 min; [M+H]+=338.0.

Workup

  1. customThe mixture was evaporated in vacuo
  2. customthe residue was purified by prep HPLC (Macherey-Nagel Nucleosil 250×40 mm, 5 to 100% ACN and 0.1% TFA, flow 40ml/min)
  3. additionAq. NaHCO3-solution was added to the product
  4. additioncontaining fractions
  5. customafter evaporation the aq. layer
  6. extractionwas extracted with ethyl acetate
  7. dry with materialThe organic layer was dried over MgSO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-180fe04b02904f16bc8f61079f8f5a1b
Source dataset
uspto-grants-2016_03
Patent number
US09290485B2

Reaction notes

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