Thiazolidinedione → HCID 11530238, compound

HRID 556437Notes

Reaction equation

HRID 556437 reaction equation
[S:1]1[CH2:5][C:4](=[O:6])[NH:3][C:2]1=[O:7].N1CCCC1.[N:13]1([C:19]2[C:20]3[N:28]=[C:27]([CH:29]=O)[CH:26]=[CH:25][C:21]=3[N:22]=[CH:23][N:24]=2)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1>CO>[N:13]1([C:19]2[C:20]3[N:28]=[C:27](/[CH:29]=[C:5]4/[C:4](=[O:6])[NH:3][C:2](=[O:7])[S:1]/4)[CH:26]=[CH:25][C:21]=3[N:22]=[CH:23][N:24]=2)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

5

Reactant 3

HCID 5437ThiazolidinedioneHCID 31268PyrrolidineHCID 11630104HCID 11630104, compound2×

Product 1

HCID 11530238HCID 11530238, compoundYield 48.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
70 °C

Procedure

A mixture of 2,4-thiazolidinedione (3.4 g; 29.1 mmol; 1.80 eq.), pyrrolidine (269.80 μL; 3.2 mmol; 0.2 eq.) in MeOH (50 mL) was heated at 70° C. A solution of 4-(1-piperidinyl)pyrido[3,2-d]pyrimidine-6-carbaldehyde (Intermediate 1.7) (3.9 g; 16.2 mmol; 1 eq.) in MeOH (50 mL) was slowly added over 1.5 hour at 70° C. After 2 h under reflux after the addition, the reaction was complete. A precipitate was formed. The hot reaction mixture was filtered and the solid was washed with cold MeOH to give (5Z)-5-{[4-(1-piperidinyl)pyrido[3,2-d]pyrimidin-6-yl]methylene}-1,3-thiazolidine-2,4-dione (1) (2.70 g; 48%) as an orange powder in 98% HPLC purity.

Workup

  1. temperatureAfter 2 h under reflux
  2. additionafter the addition
  3. customA precipitate was formed
  4. filtrationThe hot reaction mixture was filtered
  5. washthe solid was washed with cold MeOH

Sources & evidence

ORD record
ord-ed5c73411f904ed59d7f6d000c867ad6
Source dataset
uspto-grants-2011_11
Patent number
US08058289B2

Reaction notes

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