p-Toluenesulfonic acid monohydrate → HCID 59311461, compound

HRID 1693265Notes

Reaction equation

HRID 1693265 reaction equation
O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[Cl:13][C:14]1[N:19]=[C:18]([N:20]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[N:17]=[C:16]2[N:35]([CH2:46][C:47]3[C:52]([CH3:53])=[C:51]([O:54][CH3:55])[C:50]([CH3:56])=[CH:49][N:48]=3)[N:36]=[C:37]([CH2:38][CH:39]3[CH2:43][O:42]C(C)(C)[O:40]3)[C:15]=12>CO.[Cl-].[Na+].O>[Cl:13][C:14]1[N:19]=[C:18]([N:20]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[C:21]([O:23][C:24]([CH3:25])([CH3:27])[CH3:26])=[O:22])[N:17]=[C:16]2[N:35]([CH2:46][C:47]3[C:52]([CH3:53])=[C:51]([O:54][CH3:55])[C:50]([CH3:56])=[CH:49][N:48]=3)[N:36]=[C:37]([CH2:38][CH:39]([OH:40])[CH2:43][OH:42])[C:15]=12

Participants

5

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 59311582HCID 59311582, compound

Product 1

HCID 59311461HCID 59311461, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

p-Toluenesulfonic acid monohydrate (3.76 g) was added to a solution of di-tert-butyl {4-chloro-3-[(2,2-dimethyl-1,3-dioxolan-4-yl)methyl]-1-[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]-1H-pyrazolo[3,4-d]pyrimidin-6-yl}imidodicarbonate of 6) above (12.52 g) in methanol (250 mL), and the mixture was stirred at room temperature for seven hours. The reaction mixture was poured into brine, followed by extraction with ethyl acetate. The organic layer was washed with brine, and then dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate-methanol) to obtain the title compound (9.64 g, 82%) as an amorphous substance.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationAfter filtration
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate-methanol)

Sources & evidence

ORD record
ord-c46f35fbb8d5498588b1ef1536f4e7ee
Source dataset
uspto-grants-2012_04
Patent number
US08158638B2

Reaction notes

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