Thiazolidinedione → 1-(4-((2,4-Dioxothiazolidin-3-yl)methyl)thiazol-2-yl)-3-(3-fluorobenzyl)urea

HRID 1685086Notes

Reaction equation

HRID 1685086 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][CH:19]=1)[CH2:5][NH:6][C:7]([NH:9][C:10]1[S:11][CH:12]=[C:13]([CH2:15]I)[N:14]=1)=[O:8].CCN(C(C)C)C(C)C.C(=O)([O-])[O-].[K+].[K+].[S:35]1[CH2:39][C:38](=[O:40])[NH:37][C:36]1=[O:41]>C1COCC1>[O:41]=[C:36]1[N:37]([CH2:15][C:13]2[N:14]=[C:10]([NH:9][C:7]([NH:6][CH2:5][C:4]3[CH:17]=[CH:18][CH:19]=[C:2]([F:1])[CH:3]=3)=[O:8])[S:11][CH:12]=2)[C:38](=[O:40])[CH2:39][S:35]1

Participants

6

Reactant 4

HCID 5437ThiazolidinedioneHCID 11430Potassium CarbonateHCID 81531DiisopropylethylamineHCID 580550601-(3-Fluorobenzyl)-3-(4-(iodomethyl)thiazol-2-yl)urea2×

Product 1

HCID 252074361-(4-((2,4-Dioxothiazolidin-3-yl)methyl)thiazol-2-yl)-3-(3-fluorobenzyl)urea

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-(3-Fluoro-benzyl)-3-(4-iodomethyl-thiazol-2-yl)-urea (Intermediate 7, 0.3 mmol) was taken up in THF (3 ml) and DIPEA (1 eq.) and potassium carbonate (1 eq.) was added, followed by thiazolidine-2,4-dione (1 eq.). The reaction was stirred at room temperature overnight. Solvent is removed in vacuo and the crude material was purified by column chromatography with a gradient of 0-60% of (9:1 EtOAc/MeOH) and hexanes to afford 1-(4-((2,4-dioxothiazolidin-3-yl)methyl)thiazol-2-yl)-3-(3-fluorobenzyl)urea (EX #109) as a white solid.

Workup

  1. customSolvent is removed in vacuo
  2. customthe crude material was purified by column chromatography with a gradient of 0-60% of (9:1 EtOAc/MeOH) and hexanes

Sources & evidence

ORD record
ord-ab3bfc4167f245a6896567cb5e07b132
Source dataset
uspto-grants-2012_04
Patent number
US08148380B2

Reaction notes

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