Pyruvic Acid → Mitoglitazone

HRID 1844493Notes

Reaction equation

HRID 1844493 reaction equation
[CH2:1]([C:3]1[CH:4]=[CH:5][C:6](/[C:9](=N/OC)/[CH2:10][O:11][C:12]2[CH:25]=[CH:24][C:15]([CH2:16][CH:17]3[S:21][C:20](=[O:22])[NH:19][C:18]3=[O:23])=[CH:14][CH:13]=2)=[N:7][CH:8]=1)[CH3:2].C(O)(=O)C(C)=[O:31]>Cl>[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]([C:9](=[O:31])[CH2:10][O:11][C:12]2[CH:25]=[CH:24][C:15]([CH2:16][CH:17]3[S:21][C:20](=[O:22])[NH:19][C:18]3=[O:23])=[CH:14][CH:13]=2)=[N:7][CH:8]=1)[CH3:2]

Participants

4

Reactant 2

HCID 1060Pyruvic AcidHCID 56835831HCID 56835831, compound

Product 1

HCID 10429242Mitoglitazone

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A stirring solution of 5-(4-{[(2Z)-2-(5-ethylpyridin-2-yl)-2-(methoxyimino)ethyl]oxy}benzyl)-1,3-thiazolidine-2,4-dione (81 mg, 0.20 mmol; Supplier=Kalexsyn; Lot=1003-TTP-194) in 6M HCl (2 ml) and pyruvic acid (0.5 ml) was heated at 75° C. After 2 h at 75° C. HPLC showed reaction was complete. Neutralized with sat'd NaHCO3 and extracted with EtOAc. Extract dried (Na2SO4), filtered and evaporated in vacuo to give 45 mg (60%) pale yellow oil. 1H-NMR (DMSO-d6): δ12.02 (brs, 1H), 8.64 (s, 1H), 7.91 (m, 1H), 7.14 (d, J=8.5 Hz, 2H), 6.88 (d, J=8.5 Hz, 2H), 5.66 (s, 2H), 4.87 (dd, J=9.2, 4.3 Hz, 1H), 3.31 (m, 1H), 3.05 (dd, J=14.1, 9.1 Hz, 1H), 2.74 (q, J=7.7 Hz, 2H), 1.23 (t, J=7.7 Hz, 3H). HPLC (3.860 min., 100area % @ 210 and 254 nm. MS (ESI−) for C19H18N2O4S m/z 371.3 (M+H)+; m/z 369.4 (M−H)−

Workup

  1. customreaction
  2. extractionNeutralized with sat'd NaHCO3 and extracted with EtOAc
  3. extractionExtract
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customto give 45 mg (60%)
  8. custom3.860 min., 100area

Sources & evidence

ORD record
ord-bc4b1bb186ed467cb2faac49f7fd2f6d
Source dataset
uspto-grants-2015_02
Patent number
US08946435B2

Reaction notes

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