Beta-Alanine → 5-[4-(1,4-Dioxa-8-aza-spiro[4.5]dec-8-yl)-3-fluoro-benzylidene]-thiazolidine-2,4-dione

HRID 1061230Notes

Reaction equation

HRID 1061230 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][N:8]([C:11]3[CH:18]=[CH:17][C:14]([CH:15]=O)=[CH:13][C:12]=3[F:19])[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.[S:20]1[CH2:24][C:23](=[O:25])[NH:22][C:21]1=[O:26].NCCC(O)=O>>[O:1]1[C:5]2([CH2:10][CH2:9][N:8]([C:11]3[CH:18]=[CH:17][C:14]([CH:15]=[C:24]4[S:20][C:21](=[O:26])[NH:22][C:23]4=[O:25])=[CH:13][C:12]=3[F:19])[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1

Participants

4

Reactant 3

HCID 239Beta-AlanineHCID 5437ThiazolidinedioneHCID 222204894-(1,4-Dioxa-8-aza-spiro[4.5]dec-8-yl)-3-fluoro-benzaldehyde

Product 1

HCID 867588575-[4-(1,4-Dioxa-8-aza-spiro[4.5]dec-8-yl)-3-fluoro-benzylidene]-thiazolidine-2,4-dione

Procedure

The title compound was prepared from 4-(1,4-dioxa-8-aza-spiro[4.5]dec-8-yl)-3-fluoro-benzaldehyde (which was obtained in Example 59), 2,4 thiazolidinedione and β-alanine according to the procedure of Example 33 as an orange solid; mp 159-160° C.; 1H NMR (300 MHz, CDCl3) δ 7.01 (m, 1H), 7.13-7.22 (m, 2H), 7.71-7.77 (m, 1H); MS (ES) m/z: 363.3 (M−H)−.

Sources & evidence

ORD record
ord-e6b54091a3c74bb981467868e31f7db0
Source dataset
uspto-grants-2003_02
Patent number
US06525202B2

Reaction notes

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