Ethanol → HCID 68432345, compound

HRID 2092078Notes

Reaction equation

HRID 2092078 reaction equation
[CH3:1][S:2][C:3]1[C:8](=[O:9])[N:7]([CH2:10][C:11]([OH:13])=[O:12])[N:6]=[CH:5][C:4]=1[NH:14][C@@H:15]1[CH2:20][C@@H:19]2[CH2:21][C@@H:17]([C:18]2([CH3:23])[CH3:22])[C@H:16]1[CH3:24].[CH2:25](O)[CH3:26].C(OCC)(=O)C>O1CCCC1>[CH3:1][S:2][C:3]1[C:8](=[O:9])[N:7]([CH2:10][C:11]([O:13][CH2:25][CH3:26])=[O:12])[N:6]=[CH:5][C:4]=1[NH:14][C@@H:15]1[CH2:20][C@@H:19]2[CH2:21][C@@H:17]([C:18]2([CH3:23])[CH3:22])[C@H:16]1[CH3:24]

Participants

5

Reactant 3

HCID 702EthanolHCID 8857Ethyl AcetateHCID 68431485HCID 68431485, compound

Product 1

HCID 68432345HCID 68432345, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-{5-Methylthio-6-oxo-4-[(1R,2R,3R,5S)-2,6,6-trimethylbicyclo[3.1.1]hept-3-ylamino]pyridazin-1(6H)-yl}acetic acid (105 mg, 0.299 mmol) in tetrahydrofuran (1 mL) was stirred with 1,1-carbonyldiimidazole (145 mg, 0.897 mmol) at room temperature for 1 hour and then with ethanol (0.2 mL) at room temperature for 1 hour. After completion of the reaction, ethyl acetate was added, and the resulting organic layer was washed with 1 M hydrochloric acid and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate. The resulting residue was purified by silica gel chromatography (hexane/ethyl acetate=1/1) to give the desired product (93 mg, 82% yield).

Workup

  1. additionwas added
  2. washthe resulting organic layer was washed with 1 M hydrochloric acid and saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe resulting residue was purified by silica gel chromatography (hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-2536aa2eb13c4d26aaf98ed351fa14a7
Source dataset
uspto-grants-2013_05
Patent number
US08440666B2

Reaction notes

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