Piperidine → HCID 131735923, compound

HRID 2207527Notes

Reaction equation

HRID 2207527 reaction equation
NC1N=CN=C2N(CCC[N:27]3[C:31](=[O:32])[CH2:30][S:29][C:28]3=[O:33])N=C(C3C=CC(OC4C=CC=CC=4)=CC=3)C=12.[CH:34]1([CH:37]=O)[CH2:36][CH2:35]1.N1CCCCC1>C(O)C>[CH:34]1([CH:37]=[C:30]2[S:29][C:28](=[O:33])[NH:27][C:31]2=[O:32])[CH2:36][CH2:35]1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 123114CyclopropanecarboxaldehydeHCID 89189103HCID 89189103, compound

Product 1

HCID 131735923HCID 131735923, compoundYield 68.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3-(3-(4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)propyl)thiazolidine-2,4-dione (0.20 g, 0.43 mmol), cyclopropanecarbaldehyde (91 mg, 1.3 mmol, 3.0 eq.) and a drop of piperidine in ethanol (15 mL) was refluxed overnight. The volatile phase was removed under reduced pressure. The residue was applied on silica gel and eluted with petroleum:ethyl acetate (3:2) to give 3-(3-(4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)propyl)-5-(cyclopropylmethylene thiazolidine-2,4-dione (50 mg) as a white solid. MS (ESI, pos. ion) m/z: 513 (M+1)

Workup

  1. customThe volatile phase was removed under reduced pressure
  2. washeluted with petroleum:ethyl acetate (3:2)

Sources & evidence

ORD record
ord-91eb2bae6740462cb5ff584fec924600
Source dataset
uspto-grants-2016_06
Patent number
US09376438B2

Reaction notes

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