p-Toluenesulfonic acid → HCID 54759649, compound

HRID 467781Notes

Reaction equation

HRID 467781 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-b4273c36cbdd431f8ffe6b3bd1f65991
Source dataset
uspto-grants-2014_01
Patent number
US08623866B2

Reaction notes

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