p-Toluenesulfonic acid → HCID 54759649, compound

HRID 2368378Notes

Reaction equation

HRID 2368378 reaction equation
[CH:1]1([C:4]2[N:9]=[C:8]([C:10]([NH:12][C:13]3[CH:14]=[N:15][N:16]([CH2:22][CH2:23][O:24]C4CCCCO4)[C:17]=3[C:18](=[O:21])[NH:19][CH3:20])=[O:11])[C:7]([NH:31][C:32]3[CH:33]=[N:34][CH:35]=[N:36][CH:37]=3)=[N:6][CH:5]=2)[CH2:3][CH2:2]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[OH:24][CH2:23][CH2:22][N:16]1[C:17]([C:18](=[O:21])[NH:19][CH3:20])=[C:13]([NH:12][C:10]([C:8]2[C:7]([NH:31][C:32]3[CH:33]=[N:34][CH:35]=[N:36][CH:37]=3)=[N:6][CH:5]=[C:4]([CH:1]3[CH2:3][CH2:2]3)[N:9]=2)=[O:11])[CH:14]=[N:15]1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 70116520HCID 70116520, compound

Product 1

HCID 54759649HCID 54759649, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 6-cyclopropyl-N-(5-(methylcarbamoyl)-1-(2-(tetrahydro-2H-pyran-2-yloxy)ethyl)-1H-pyrazol-4-yl)-3-(pyrimidin-5-ylamino)pyrazine-2-carboxamide (0.07 g, 138 μmol, Eq: 1.00) at r.t under Ar in MeOH (2.7 ml) was added a amount catalytic amount of para-toluene sulfonic acid. The mixture was stirred at 70° for 1 hr. The solvent was evaporated. The residue was dissolved in dichloromethane, then washed with water. The organic was dried over MgSO4, filtered and evaporated. The crude product was purified by silica gel chromatography using a dichloromethane/MeOH gradient to obtain the tile compound (53 mg, 91%) as yellow solid.

Workup

  1. customThe solvent was evaporated
  2. dissolutionThe residue was dissolved in dichloromethane
  3. washwashed with water
  4. dry with materialThe organic was dried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-10b31c3a6ce04c20b691a38b8bc4e852
Source dataset
uspto-grants-2014_04
Patent number
US08703768B2

Reaction notes

Loading…