Hydrochloric Acid → HCID 59026779, compound

HRID 658381Notes

Reaction equation

HRID 658381 reaction equation
C(OC([C:6]1[O:7][C:8]([C:11]2[CH:16]=[CH:15][N:14]=[CH:13][C:12]=2[NH:17][C:18]2[CH:23]=[CH:22][C:21]([I:24])=[CH:20][C:19]=2[F:25])=[N:9][N:10]=1)=O)C.[Li+].[OH-].Cl>C1COCC1.O>[F:25][C:19]1[CH:20]=[C:21]([I:24])[CH:22]=[CH:23][C:18]=1[NH:17][C:12]1[CH:13]=[N:14][CH:15]=[CH:16][C:11]=1[C:8]1[O:7][CH:6]=[N:10][N:9]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 59026806HCID 59026806, compound

Product 1

HCID 59026779HCID 59026779, compoundYield 52.9%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a solution of 5-[3-(2-Fluoro-4-iodo-phenylamino)-pyridin-4-yl]-[1,3,4]oxadiazole-2-carboxylic acid ethyl ester (200 mg, 0.44 mmol) in THF-H2O (1:1)(5 mL) LiOH (32 mg, 1.32 mmol) was added. The reaction mixture was stirred for 2 hrs and then the pH was adjusted to 5 with 1N HCl. Upon dilution with water a solid precipitated. Filtration afforded the desired product (89 mg). LC/MS (Method A) [0.48 min; 383(M+1)]

Workup

  1. customUpon dilution with water a solid precipitated
  2. filtrationFiltration

Sources & evidence

ORD record
ord-5af274d79eaf4c89964962f380f528eb
Source dataset
uspto-grants-2011_12
Patent number
US08076486B2

Reaction notes

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