Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 58201194, compound

HRID 1693321Notes

Reaction equation

HRID 1693321 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([N:8]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[N:5]=[C:4]2[N:23]([CH2:34][C:35]3[CH:40]=[CH:39][C:38]([O:41][CH3:42])=[CH:37][CH:36]=3)[N:24]=[C:25]([CH2:26][CH:27]3[CH2:31][O:30]C(C)(C)[O:28]3)[C:3]=12.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>CO>[Cl:1][C:2]1[N:7]=[C:6]([N:8]([C:16]([O:18][C:19]([CH3:20])([CH3:21])[CH3:22])=[O:17])[C:9]([O:11][C:12]([CH3:14])([CH3:15])[CH3:13])=[O:10])[N:5]=[C:4]2[N:23]([CH2:34][C:35]3[CH:36]=[CH:37][C:38]([O:41][CH3:42])=[CH:39][CH:40]=3)[N:24]=[C:25]([CH2:26][CH:27]([OH:28])[CH2:31][OH:30])[C:3]=12

Participants

4

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 58201211HCID 58201211, compound

Product 1

HCID 58201194HCID 58201194, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The above di-tert-butyl {4-chloro-3-[(2,2-dimethyl-1,3-dioxolan-4-yl)methyl]-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-d]pyrimidin-6-yl}imidodicarbonate (22 g) was dissolved in methanol (400 ml). Pyridinium p-toluenesulfonate (10 g) was added and the mixture was stirred at room temperature for 16 hours. The reaction solution was concentrated, and water (100 ml) was added to the resulting residue, followed by extraction with ethyl acetate (500 ml). The organic layer was washed with brine, and then dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure to obtain the title compound (19.5 g, 95%) as an amorphous.

Workup

  1. concentrationThe reaction solution was concentrated
  2. additionwater (100 ml) was added to the resulting residue
  3. extractionfollowed by extraction with ethyl acetate (500 ml)
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationAfter filtration
  7. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-c75d0952e92d4a9b9ed8576ebc50a9c6
Source dataset
uspto-grants-2012_04
Patent number
US08158638B2

Reaction notes

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