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

HRID 716039Notes

Reaction equation

HRID 716039 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].[S:33]1[CH2:37][C:36](=[O:38])[NH:35][C:34]1=[O:39].C(O)(=O)C.N1CCCCC1>C(O)C>[C:1]([C:7]1[C:15]2[C:10](=[N:11][CH:12]=[C:13]([NH:16][C:17]3[CH:18]=[CH:19][C:20]([CH:21]=[C:37]4[S:33][C:34](=[O:39])[NH:35][C:36]4=[O:38])=[CH:23][CH:24]=3)[N:14]=2)[N:9]([CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:31])([CH3:32])[CH3:30])[CH:8]=1)(=[O:6])[C:2]([CH3:4])([CH3:3])[CH3:5]

Participants

5

Reactant 3

HCID 5437ThiazolidinedioneHCID 9793820Piperidine, acetateHCID 867121234-(7-pivaloyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-ylamino)benzaldehyde

Product 1

HCID 867121265-(4-(7-pivaloyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-ylamino)benzylidene)thiazolidine-2,4-dioneYield 77%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
80 °C

Procedure

To a 35 ml reaction vial 4-(7-pivaloyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl amino)benzaldehyde (0.200 g, 0.0004 mole) and thiazolidine-2,4-dione (0.155 g, 0.0105 mole) were taken in ethanol (10 ml). Piperidine acetate (3.3M solution in water) (3 ml) was added at RT. The reaction mixture was heated to 80° C. for 16 hrs. After completion of the reaction, ethanol was evaporated under reduced pressure and diluted with EtOAc. Organic layer was washed with water, dried over Na2SO4 and evaporated to get crude product which was purified using column purification by eluting the compound with 10-20% EtOAc in Hexanes to yield 0.170 g of 5-(4-(7-pivaloyl-5-((2-(trimethylsilyl)ethoxy)-methyl)-5H-pyrrolo[2,3-b]pyrazin-2-ylamino)benzylidene)thiazolidine-2,4-dione.

Workup

  1. customwas evaporated under reduced pressure
  2. additiondiluted with EtOAc
  3. washOrganic layer was washed with water
  4. dry with materialdried over Na2SO4
  5. customevaporated
  6. customto get crude product which
  7. customwas purified
  8. customcolumn purification
  9. washby eluting the compound with 10-20% EtOAc in Hexanes

Sources & evidence

ORD record
ord-652b8cc4465d4176a8740beb215fe18a
Source dataset
uspto-grants-2015_11
Patent number
US09187487B2

Reaction notes

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