Pioglitazone → HCID 54751748, compound

HRID 2368762Notes

Reaction equation

HRID 2368762 reaction equation
[N+:1]([O:4][CH2:5][CH2:6][NH:7][C:8](=[O:12])[O:9][CH2:10]Cl)([O-:3])=[O:2].[CH2:13]([C:15]1[CH:16]=[CH:17][C:18]([CH2:21][CH2:22][O:23][C:24]2[CH:37]=[CH:36][C:27]([CH2:28][CH:29]3[S:33][C:32](=[O:34])[NH:31][C:30]3=[O:35])=[CH:26][CH:25]=2)=[N:19][CH:20]=1)[CH3:14].C(N(CC)CC)C>C(Cl)Cl.O>[N+:1]([O:4][CH2:5][CH2:6][NH:7][C:8](=[O:12])[O:9][CH2:10][N:31]1[C:30](=[O:35])[CH:29]([CH2:28][C:27]2[CH:36]=[CH:37][C:24]([O:23][CH2:22][CH2:21][C:18]3[CH:17]=[CH:16][C:15]([CH2:13][CH3:14])=[CH:20][N:19]=3)=[CH:25][CH:26]=2)[S:33][C:32]1=[O:34])([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 4829PioglitazoneHCID 8471TriethylamineHCID 86679074HCID 86679074, compound

Product 1

HCID 54751748HCID 54751748, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent3×

Procedure

A solution of chloromethyl 2-(nitrooxy)ethylcarbamate (2, 13.37 g, 67.3 mmol) in CH2Cl2 (20 ml) is added drop-wise to a suspension of 5-(4-(2-(5-ethylpyridin-2-yl)ethoxy)benzyl)-thiazolidine-2,4-dione (pioglitazone, 12 g, 33.7 mmol) in CH2Cl2 (160 ml) and triethylamine (9.38 ml, 67.3 mmol) at 22° C. (room temperature) under an argon atmosphere. The reaction is stirred for 8 h. The reaction is diluted with CH2Cl2 and H2O and the layers separated. The organic layer is dried (MgSO4) and the solvent evaporated to give the crude product. The crude material is purified by column chromatography (silica, 40:60 ethyl acetate:heptane, product Rf 0.3 (80:20 ethyl acetate:heptane) to give the title compound (5-(4-(2-(5-ethylpyridin-2-yl)ethoxy)benzyl)-2,4-dioxothiazolidin-3-yl)methyl 2-(nitrooxy)ethylcarbamate (1), 5.3 g (30%), as a white solid.

Workup

  1. customthe layers separated
  2. dry with materialThe organic layer is dried (MgSO4)
  3. customthe solvent evaporated
  4. customto give the crude product
  5. customThe crude material is purified by column chromatography (silica, 40:60 ethyl acetate

Sources & evidence

ORD record
ord-f7d038e3a629472b8da1e1c74eca354d
Source dataset
uspto-grants-2014_04
Patent number
US08703800B2

Reaction notes

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