Beta-Alanine → HCID 131731769, compound

HRID 1747202Notes

Reaction equation

HRID 1747202 reaction equation
[O:1]1CC[O:3][CH:2]1[C:6]1[CH:7]=[C:8]([NH:12][C:13]2[S:14][CH:15]=[C:16]([C:18]3[S:22][C:21]([NH:23][C:24](=[O:26])[CH3:25])=[N:20][C:19]=3[CH3:27])[N:17]=2)[CH:9]=[CH:10][CH:11]=1.[S:28]1[CH2:32][C:31](=[O:33])[NH:30][C:29]1=[O:34].NCCC(O)=O.O>CC(O)=O>[C:2]([OH:3])(=[O:1])[CH3:6].[O:34]=[C:29]1[NH:30][C:31](=[O:33])/[C:32](=[CH:2]/[C:6]2[CH:7]=[C:8]([NH:12][C:13]3[S:14][CH:15]=[C:16]([C:18]4[S:22][C:21]([NH:23][C:24](=[O:26])[CH3:25])=[N:20][C:19]=4[CH3:27])[N:17]=3)[CH:9]=[CH:10][CH:11]=2)/[S:28]1

Participants

6

Reactant 4

HCID 239Beta-AlanineHCID 962WaterHCID 5437ThiazolidinedioneHCID 86626619HCID 86626619, compound

Product 1

HCID 131731769HCID 131731769, compoundYield 9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

A solution of N-(2-{[3-(1,3-dioxolan-2-yl)phenyl]amino}-4′-methyl-4,5′-bi-1,3-thiazol-2′-yl)acetamide obtained in Step 1 as described above (290.00 mg; 0.72 mmol; 1.00 eq.), 2,4-thiazolidinedione (151.90 mg; 1.30 mmol; 1.80 eq.) and beta-alanine (115.55 mg; 1.30 mmol; 1.80 eq.) in AcOH (6.00 ml) are heated at 100° C. for 1 h30. Water is added and the precipitate is filtered and washed with Et2O, affording (62) as a yellow solid (35 mg; 9%).

Workup

  1. filtrationthe precipitate is filtered
  2. washwashed with Et2O

Sources & evidence

ORD record
ord-3ec6b157fbd14e7abe7c1824c63e5b25
Source dataset
uspto-grants-2015_10
Patent number
US09150561B2

Reaction notes

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