Lithium iodide → HCID 44443257, compound

HRID 1945436Notes

Reaction equation

HRID 1945436 reaction equation
C[O:2][C:3](=[O:31])[C:4]1[CH:9]=[C:8]([NH:10][C:11](=[O:30])[CH2:12][O:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]34[CH2:29][CH:24]5[CH2:25][CH:26]([CH2:28][CH:22]([CH2:23]5)[CH2:21]3)[CH2:27]4)=[CH:16][CH:15]=2)[CH:7]=[N:6][CH:5]=1.[I-].[Li+]>N1C=CC=CC=1>[C:20]12([C:17]3[CH:18]=[CH:19][C:14]([O:13][CH2:12][C:11]([NH:10][C:8]4[CH:7]=[N:6][CH:5]=[C:4]([CH:9]=4)[C:3]([OH:31])=[O:2])=[O:30])=[CH:15][CH:16]=3)[CH2:27][CH:26]3[CH2:28][CH:22]([CH2:23][CH:24]([CH2:25]3)[CH2:29]1)[CH2:21]2

Participants

4

Reactant 2

HCID 66321Lithium iodideHCID 24811990HCID 24811990, compound

Product 1

HCID 44443257HCID 44443257, compoundYield 33.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 5-[2-(4-adamantan-1-yl-phenoxy)acetylamino]-nicotinic acid methyl ester (50 mg, 0.11 mmol) and lithium Iodide (189 mg, 1.11 mmol) in pyridine (3 mL) was heated to reflux until reaction completion, then cooled and distilled off the solvent under reduced pressure. The residue was taken up in water, neutralized and extracted with methanol/MC mixture (10%). The combined extracts were washed with brine and water, dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. The resultant crude product was purified by HPLC (MeOH/MC-10%) to afford 5-[2-(4-adamantan-1-yl-phenoxy)-acetylamino]-nicotinic acid as a colorless solid (0.015 g, 30% yield).

Workup

  1. temperatureto reflux until reaction completion
  2. temperaturecooled
  3. distillationdistilled off the solvent under reduced pressure
  4. extractionextracted with methanol/MC mixture (10%)
  5. washThe combined extracts were washed with brine and water
  6. dry with materialdried over anhydrous MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe resultant crude product was purified by HPLC (MeOH/MC-10%)

Sources & evidence

ORD record
ord-a4bdcea1d32147b485515b757e791be8
Source dataset
uspto-grants-2013_03
Patent number
US08394799B2

Reaction notes

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