Lithium iodide → HCID 44443250, compound

HRID 1945437Notes

Reaction equation

HRID 1945437 reaction equation
C[O:2][C:3](=[O:31])[C:4]1[CH:9]=[CH:8][N:7]=[C:6]([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: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:6]4[CH:5]=[C:4]([CH:9]=[CH:8][N:7]=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 24811989HCID 24811989, compound

Product 1

HCID 44443250HCID 44443250, compoundYield 87.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 2-[2-(4-adamantan-1-yl-phenoxy)-acetylamino]-isonicotinic acid methyl ester (50 mg, 0.11 mmol) and lithium Iodide (159 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=100%) to afford 2-[2-(4-adamantan-1-yl-phenoxy)-acetylamino]-isonicotinic acid as a colorless solid (0.039 g, 81% 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=100%)

Sources & evidence

ORD record
ord-4423fdef21964e32b6bab7eaef7d1280
Source dataset
uspto-grants-2013_03
Patent number
US08394799B2

Reaction notes

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