Hydrochloric Acid → HCID 76416798, compound

HRID 341132Notes

Reaction equation

HRID 341132 reaction equation
[OH:1][C:2]1[CH:15]=[CH:14][C:5]([CH2:6][CH:7]2[S:11][C:10](=[O:12])[NH:9][C:8]2=[O:13])=[CH:4][CH:3]=1.CC(C)([O-])C.[K+].[CH3:22][O:23]/[N:24]=[C:25](/[C:28]1[CH:33]=[CH:32][C:31]([CH2:34][CH3:35])=[CH:30][N:29]=1)\[CH2:26]Br.Cl>CS(C)=O>[CH2:34]([C:31]1[CH:32]=[CH:33][C:28]([C:25](=[N:24][O:23][CH3:22])[CH2:26][O:1][C:2]2[CH:15]=[CH:14][C:5]([CH2:6][CH:7]3[S:11][C:10](=[O:12])[NH:9][C:8]3=[O:13])=[CH:4][CH:3]=2)=[N:29][CH:30]=1)[CH3:35]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 101983975-(4-Hydroxybenzyl)thiazolidine-2,4-dioneHCID 23665647Potassium tert-butoxideHCID 89735788HCID 89735788, compound

Product 1

HCID 76416798HCID 76416798, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

To a stirring solution of 5-(4-hydroxybenzyl)thiazolidine-2,4-dione (210 mg, 0.941 mmol) in DMSO was added potassium tert-Butoxide (227 mg, 2.02 mmol) in a single portion. Stirred at RT for 15 minutes. Added a solution of (1Z)-2-bromo-1-(5-ethylpyridin-2-yl)ethanone O-methyloxime (242 mg, 0.941 mmol; Supplier=Kalexsyn; Lot=1003-TTP-186) in DMSO (2 ml). Added 1M HCl until pH of mixture was about 3. Extracted with EtOAc. The extract was washed with water, dried (Na2SO4), filtered and evaporated in vacuo to give an off-white foam. 278 mg. 1H-NMR (DMSO-d6): δ12.05 (brs, 1H), 8.47 (d, J=1.7 Hz, 1H), 7.77 (m, 1H), 7.70 m, 1H), 7.14 (d, J=8.5 Hz, 2H), 6.90 (d, J=8.5 Hz, 2H), 5.17 (s, 2H), 4.87 (dd, J=8.9, 4.4 Hz, 1H), 4.01 (s, 3H), 3.30 (dd, J=14.2, 4.5 Hz, 1H), 3.06 (dd, J=14.1, 9.1 Hz, 1H), 2.64 (q, J=7.7 Hz, 2H), 1.19 (t, J=7.6 Hz, 3H). HPLC: 3.103 min., 82 area % and 3.379 min., 18 area % @254 nm; 3.109 min., 91 area % and 3.379 min., 9 area % @ 254 nm. MS (ESI—) for C20H21N3O4S m/z 400.3 (M+H)+: m/z 398.3 (M−H)−

Workup

  1. extractionExtracted with EtOAc
  2. washThe extract was washed with water
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customto give an off-white foam
  7. custom3.103 min., 82 area
  8. custom3.379 min., 18 area
  9. custom3.109 min., 91 area
  10. custom3.379 min., 9 area

Sources & evidence

ORD record
ord-14b119d2610d4e51beeef84357d61fed
Source dataset
uspto-grants-2014_11
Patent number
US08895748B2

Reaction notes

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