p-Toluenesulfonic acid monohydrate → HCID 90025929, compound

HRID 1055015Notes

Reaction equation

HRID 1055015 reaction equation
[CH3:1][C:2]1[N:7]2[N:8]=[C:9]([CH2:11][CH2:12][C:13]3[N:17]([CH3:18])[N:16]=[C:15]([N:19]4[CH2:23][CH2:22][CH:21]([O:24]C5CCCCO5)[CH2:20]4)[N:14]=3)[N:10]=[C:6]2[C:5]([CH3:31])=[N:4][CH:3]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[CH3:1][C:2]1[N:7]2[N:8]=[C:9]([CH2:11][CH2:12][C:13]3[N:17]([CH3:18])[N:16]=[C:15]([N:19]4[CH2:23][CH2:22][CH:21]([OH:24])[CH2:20]4)[N:14]=3)[N:10]=[C:6]2[C:5]([CH3:31])=[N:4][CH:3]=1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrate2×HCID 90025276HCID 90025276, compound

Product 1

HCID 90025929HCID 90025929, compoundYield 8.51%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 5,8-dimethyl-2-(2-(1-methyl-3-(3-(tetrahydro-2H-pyran-2-yloxy)pyrrolidin-1-yl)-1H-1,2,4-triazol-5-yl)ethyl)-[1,2,4]triazolo[1,5-a]pyrazine (30 mg, 70.3 μmol, Eq: 1.00) in methanol (3 ml) was added p-toluenesulfonic acid monohydrate (669 μg, 3.52 μmol, Eq: 0.05), the resulting mixture was stirred for 2 hours at 25° C. under nitrogen atmosphere→nearly no reaction, another portion of p-toluenesulfonic acid monohydrate (13.4 mg, 70.3 μmol, Eq: 1.00) was added, stirring at 25° C. was continued overnight. The solvent was evaporated. The residue was diluted with ethyl acetate and washed with sat. sodium hydrogen carbonate. The organic layer was separated, dried over magnesium sulfate, filtrated and evaporated. Purification by HPLC separation afforded 1-{5-[2-(5,8-dimethyl-[1,2,4]triazolo[1,5-a]pyrazin-2-yl)-ethyl]-1-methyl-1H-[1,2,4]triazol-3-yl}-pyrrolidin-3-ol (2.05 mg, 8.51%) as a light yellow viscous oil. MS: m/z=323.5 (M+H+)

Workup

  1. customno reaction
  2. stirringstirring at 25° C.
  3. waitwas continued overnight
  4. customThe solvent was evaporated
  5. additionThe residue was diluted with ethyl acetate
  6. washwashed with sat. sodium hydrogen carbonate
  7. customThe organic layer was separated
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltrated
  10. customevaporated
  11. customPurification
  12. customby HPLC separation

Sources & evidence

ORD record
ord-80ba4ffed9db439391bf7318147141aa
Source dataset
uspto-grants-2016_07
Patent number
US09394311B2

Reaction notes

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