3-Ethyl-2,4-thiazolidinedione → 3-ethyl-5-(4-(7-pivaloyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-ylamino)benzylidene)thiazolidine-2,4-dione

HRID 716057Notes

Reaction equation

HRID 716057 reaction equation
[C:1]([C:7]1[C:15]2[C:10](=[N:11][CH:12]=[C:13]([NH:16][C:17]3[CH:24]=[CH:23][C:20]([CH:21]=O)=[CH:19][CH:18]=3)[N:14]=2)[N:9]([CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:32])([CH3:31])[CH3:30])[CH:8]=1)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[CH2:33]([N:35]1[C:39](=[O:40])[CH2:38][S:37][C:36]1=[O:41])[CH3:34].C(O)(=O)C.N1CCCCC1>C(O)C>[CH2:33]([N:35]1[C:39](=[O:40])[C:38](=[CH:21][C:20]2[CH:19]=[CH:18][C:17]([NH:16][C:13]3[N:14]=[C:15]4[C:7]([C:1](=[O:6])[C:2]([CH3:5])([CH3:3])[CH3:4])=[CH:8][N:9]([CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:32])([CH3:31])[CH3:30])[C:10]4=[N:11][CH:12]=3)=[CH:24][CH:23]=2)[S:37][C:36]1=[O:41])[CH3:34]

Participants

5

Reactant 3

HCID 51680513-Ethyl-2,4-thiazolidinedioneHCID 9793820Piperidine, acetateHCID 867121234-(7-pivaloyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-ylamino)benzaldehyde

Product 1

HCID 867121313-ethyl-5-(4-(7-pivaloyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-ylamino)benzylidene)thiazolidine-2,4-dioneYield 52.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a 50 ml three necked round bottom flask, 4-(7-pivaloyl-5-((2-(trimethylsilyl)-ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-2-ylamino)benzaldehyde (0.104 g, 0.00023 mole) and 3-ethylthiazolidine-2,4-dione (0.067 g, 0.00046 mole) was taken in ethanol (3 ml). Piperidine acetate (3.3 M solution in water) (0.1 ml) was added dropwise at RT. The reaction mixture was refluxed for 6 hrs. After completion of the reaction, ethanol was distilled out and water was added to residue. Aq. layer was extracted with ethyl acetate, the combined organic layers were dried over Na2SO4, filtered and concentrated to afford crude product which was purified by triturated with n-pentane. The solid was filtered and dried under vacuum to yield 0.070 g of 3-ethyl-5-(4-(7-pivaloyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-ylamino)benzylidene)thiazolidine-2,4-dione which was converted to the title compounds as described in Example 6 above.

Workup

  1. temperatureThe reaction mixture was refluxed for 6 hrs
  2. distillationwas distilled out and water
  3. additionwas added to residue
  4. extractionAq. layer was extracted with ethyl acetate
  5. dry with materialthe combined organic layers were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto afford crude product which
  9. customwas purified
  10. customby triturated with n-pentane
  11. filtrationThe solid was filtered
  12. customdried under vacuum

Sources & evidence

ORD record
ord-621d6b4594e744648d14122681705e6f
Source dataset
uspto-grants-2015_11
Patent number
US09187487B2

Reaction notes

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