HCID 57964943, compound → HCID 57964991, compound

HRID 1931685Notes

Reaction equation

HRID 1931685 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:18]3=[N:19][CH:20]=[N:21][C:22]([O:23][C:24]4[CH:34]=[CH:33][C:27]5[S:28](=[O:32])(=[O:31])[CH:29]=[CH:30][C:26]=5[CH:25]=4)=[C:17]3[CH:16]=[N:15]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>[Pd].C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([N:14]2[C:18]3=[N:19][CH:20]=[N:21][C:22]([O:23][C:24]4[CH:34]=[CH:33][C:27]5[S:28](=[O:31])(=[O:32])[CH2:29][CH2:30][C:26]=5[CH:25]=4)=[C:17]3[CH:16]=[N:15]2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 57964943HCID 57964943, compound

Product 1

HCID 57964991HCID 57964991, compoundYield 93.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-[4-(1,1-dioxo-1H-1λ6-benzo[b]thiophen-5-yloxy)-pyrazolo[3,4-d]pyrimidin-1-yl]-piperidine-1-carboxylic acid tert-butyl ester (Example 78; 531 mg, 1.1 mmol) and 10% palladium on carbon (50 mg) in ethyl acetate (40 mL) was stirred under an atmosphere of hydrogen for 3 h. The mixture was then filtered through Celite™ and the filtrate was evaporated and chromatographed, eluting with 50% ethyl acetate/hexanes to give 4-[4-(1,1-dioxo-2,3-dihydro-1H-1λ6-benzo[b]thiophen-5-yloxy)-pyrazolo[3,4-d]pyrimidin-1-yl]-piperidine-1-carboxylic acid tert-butyl ester (497 mg, 93%) as a white solid.

Workup

  1. filtrationThe mixture was then filtered through Celite™
  2. customthe filtrate was evaporated
  3. customchromatographed
  4. washeluting with 50% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-9ac7facdcd674735bc143236b21e23c7
Source dataset
uspto-grants-2012_05
Patent number
US08188098B2

Reaction notes

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