Hydrochloric Acid → N-(3-benzoylphenyl) N-methyl 2-(3-pyridinyl)-4-thiazolidinecarboxamide dihydrochloride

HRID 892804Notes

Reaction equation

HRID 892804 reaction equation
[ClH:1].[C:2]([C:10]1[CH:11]=[C:12]([N:16]([CH3:37])[C:17]([CH:19]2[CH2:23][S:22][CH:21]([C:24]3[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=3)[N:20]2C(OC(C)(C)C)=O)=[O:18])[CH:13]=[CH:14][CH:15]=1)(=[O:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>O1CCOCC1>[ClH:1].[ClH:1].[C:2]([C:10]1[CH:11]=[C:12]([N:16]([CH3:37])[C:17]([CH:19]2[CH2:23][S:22][CH:21]([C:24]3[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=3)[NH:20]2)=[O:18])[CH:13]=[CH:14][CH:15]=1)(=[O:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 54435265HCID 54435265, compound

Product 1

HCID 67898900N-(3-benzoylphenyl) N-methyl 2-(3-pyridinyl)-4-thiazolidinecarboxamide dihydrochlorideYield 81%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

Hydrochloric acid in dioxane (4M, 10 mL) was added to N-(3-benzoylphenyl) N-methyl 2-(3-pyridinyl)-3-tert-butoxycarbonyl-4-thiazolidinecarboxamide (0.64 g) in dioxane (3 mL). The reaction mixture was concentrated and the residue partitioned between ethyl acetate and saturated aqueous sodium carbonate. The organic layer was washed with saturated aqueous sodium carbonate and dried over magnesium sulfate. The solvent was removed in vacuo and the residue chromatographed on silica gel, eluting with ethyl acetate to give the desired compound as a colorless oil (417 mg, 81%). This was converted to the dihydrochloride salt using the method of example 3. NMR (CDCl3, 300 MHz): δ2.72-3.28 (c, 3H), 3.42-3.97 (c, 4H), 5.57 (s, 0.6H), 5.61 (s, 0.4H), 7.21-7.48 (c, 6H), 7.81 (m, 1H), 8.51 (dd, 0.4H, J=1.0, 8.0), 8.56 (dd, 0.6H, J=1.0, 8.0), 8.72 (m, 1H). Mass Spectrum (DCI/NH3): 286 (M+H)+.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue partitioned between ethyl acetate and saturated aqueous sodium carbonate
  3. washThe organic layer was washed with saturated aqueous sodium carbonate
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was removed in vacuo
  6. customthe residue chromatographed on silica gel
  7. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-7cbed40629fa4a468358e5bb9ce07512
Source dataset
uspto-grants-1992_06
Patent number
US05120751

Reaction notes

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