1,4-Dioxane → HCID 16074922, compound

HRID 1015664Notes

Reaction equation

HRID 1015664 reaction equation
[CH2:1]([NH:8][C:9]1[CH:13]=[C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[S:11][C:10]=1[C:20]([O-:22])=[O:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Na+].[CH:24]1([C:27](Cl)=[O:28])[CH2:26][CH2:25]1.O1CCOCC1>O>[CH2:1]([N:8]([C:27]([CH:24]1[CH2:26][CH2:25]1)=[O:28])[C:9]1[CH:13]=[C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[S:11][C:10]=1[C:20]([OH:22])=[O:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 312751,4-DioxaneHCID 77637Cyclopropanecarbonyl chlorideHCID 23677633HCID 23677633, compound

Product 1

HCID 16074922HCID 16074922, compoundYield 31.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of sodium 3-benzylamino-5-phenyl-thiophene-2-carboxylate (41.1 mg, 0.1 mmol) was added 32 mg (0.3 mmol) of cyclopropanecarbonyl chloride, 1.5 ml of dioxane and 0.5 ml of water. The mixture was stirred overnight at room temperature and concentrated in vacuo. A 4N hydrogen chloride solution in dioxane (1 ml) was added and the mixture was stirred for one hour at room temperature. The mixture was again concentrated and the crude material was purified by reverse phase HPLC giving access to 11.9 mg (31.5%) of 3-(benzyl-cyclopropanecarbonyl-amino)-5-phenyl-thiophene-2-carboxylic acid as a pale yellow solid. NMR 1H (DMSO D6, 400 MHz): 7.56-7.54 ppm (m, 2H, Haro); 7.39-7.13 ppm (m, 10H, Haro, Hazole and COOH); 5.27 ppm (d, 1H, J=15.2 Hz); 4.48 ppm (d, 1H, J=15.2 Hz); 1.49 ppm (m, 1H); 0.77 ppm (m, 2H); 0.61 ppm (m, 2H).

Workup

  1. concentrationconcentrated in vacuo
  2. additionA 4N hydrogen chloride solution in dioxane (1 ml) was added
  3. stirringthe mixture was stirred for one hour at room temperature
  4. concentrationThe mixture was again concentrated
  5. customthe crude material was purified by reverse phase

Sources & evidence

ORD record
ord-8d92341cff4c426a8222630fc28a7f52
Source dataset
uspto-grants-2011_07
Patent number
US07985769B2

Reaction notes

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