Trifluoroacetic acid → (S)-3-(4-methyl-6-(pyrrolidin-3-yloxy)pyridin-2-yl)-1H-1,2,4-triazol-5(4H)-one

HRID 1476915Notes

Reaction equation

HRID 1476915 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]2[NH:12][C:11](=[O:13])[NH:10][N:9]=2)[N:5]=[C:4]([O:14][C@H:15]2[CH2:19][CH2:18][N:17](C(OC(C)(C)C)=O)[CH2:16]2)[CH:3]=1.C(O)(C(F)(F)F)=O>>[CH3:1][C:2]1[CH:3]=[C:4]([O:14][C@H:15]2[CH2:19][CH2:18][NH:17][CH2:16]2)[N:5]=[C:6]([C:8]2[NH:12][C:11](=[O:13])[NH:10][N:9]=2)[CH:7]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 136596975(S)-tert-butyl 3-((4-methyl-6-(5-oxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)pyridin-2-yl)oxy)pyrrolidine-1-carboxylate

Product 1

HCID 136597090(S)-3-(4-methyl-6-(pyrrolidin-3-yloxy)pyridin-2-yl)-1H-1,2,4-triazol-5(4H)-oneYield 2.4%

Procedure

A mixture of (S)-tert-butyl 3-((4-methyl-6-(5-oxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)pyridin-2-yl)oxy)pyrrolidine-1-carboxylate (700 mg, 1.937 mmol) and TFA (3 mL, 38.9 mmol) was stirred at RT for 1 hour. The solvent was removed in vacuo and the crude product purified by preparative HPLC eluting with a gradient 5-40% ACN in water (acid mode). The product-containing fractions were collected and evaporated in vacuo to give the title compound (12 mg, 2%).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe crude product purified by preparative HPLC
  3. washeluting with a gradient 5-40% ACN in water (acid mode)
  4. customThe product-containing fractions were collected
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-846ba904989a41afaaeb7ab95eee3096
Source dataset
uspto-grants-2016_08
Patent number
US09402841B2

Reaction notes

Loading…