HCID 117777634, compound → HCID 178497269, compound

HRID 575001Notes

Reaction equation

HRID 575001 reaction equation
C([O:8][C:9]([C:11]1[CH:12]=[C:13]([C:17]2[C:25]3[C:20](=[N:21][C:22]([C:29]4[CH:30]=[CH:31][C:32]([F:39])=[C:33]([CH:38]=4)[C:34]([O:36][CH3:37])=[O:35])=[CH:23][C:24]=3[C:26](=[O:28])[NH2:27])[N:19](C3CCCCO3)[N:18]=2)[CH:14]=[CH:15][CH:16]=1)=[O:10])C1C=CC=CC=1>S(=O)(=O)(O)O>[C:26]([C:24]1[CH:23]=[C:22]([C:29]2[CH:30]=[CH:31][C:32]([F:39])=[C:33]([C:34]([O:36][CH3:37])=[O:35])[CH:38]=2)[N:21]=[C:20]2[NH:19][N:18]=[C:17]([C:13]3[CH:12]=[C:11]([CH:16]=[CH:15][CH:14]=3)[C:9]([OH:10])=[O:8])[C:25]=12)(=[O:28])[NH2:27]

Participants

3

Reactant 1

HCID 117777634HCID 117777634, compound

Product 1

HCID 178497269HCID 178497269, compoundYield 119.3%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

Methyl 5-[3-{3-[(benzyloxy)carbonyl]phenyl}-4-carbamoyl-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridin-6-yl]-2-fluorobenzoate (1.0 g/1.64 mmol) is dissolved in 6.8 mL of concentrated sulphuric acid. The solution is stirred at ambient temperature for 30 min and then run into ice-cold water and stirred for 30 min. The precipitate obtained is filtered off, washed with water and dissolved in EtOAc/MeTHF (50/50). The solution is washed with water and with a saturated aqueous solution of NaCl, dried over sodium sulphate, filtered and concentrated to dryness. The solid is taken up with a mixture of DCM/methanol, filtered and dried under vacuum to give 0.85 g of a beige powder (yield: 85%).

Workup

  1. stirringstirred for 30 min
  2. customThe precipitate obtained
  3. filtrationis filtered off
  4. washwashed with water
  5. dissolutiondissolved in EtOAc/MeTHF (50/50)
  6. washThe solution is washed with water and with a saturated aqueous solution of NaCl
  7. dry with materialdried over sodium sulphate
  8. filtrationfiltered
  9. concentrationconcentrated to dryness
  10. additionThe solid is taken up with a mixture of DCM/methanol
  11. filtrationfiltered
  12. customdried under vacuum

Sources & evidence

ORD record
ord-398169744eda46d18bc9a6547ee7ead1
Source dataset
uspto-grants-2015_05
Patent number
US09034898B2

Reaction notes

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