Hydrochloric Acid → HCID 59026786, compound

HRID 658387Notes

Reaction equation

HRID 658387 reaction equation
C([O:3][C:4](=[O:28])[CH:5]([NH:7][C:8]1[O:9][C:10]([C:13]2[CH:18]=[CH:17][N:16]=[CH:15][C:14]=2[NH:19][C:20]2[CH:25]=[CH:24][C:23]([I:26])=[CH:22][C:21]=2[F:27])=[N:11][N:12]=1)[CH3:6])C.[Li+].[OH-].Cl>C1COCC1.O.CCOC(C)=O>[F:27][C:21]1[CH:22]=[C:23]([I:26])[CH:24]=[CH:25][C:20]=1[NH:19][C:14]1[CH:15]=[N:16][CH:17]=[CH:18][C:13]=1[C:10]1[O:9][C:8]([NH:7][CH:5]([CH3:6])[C:4]([OH:28])=[O:3])=[N:12][N:11]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 59026843HCID 59026843, compound

Product 1

HCID 59026786HCID 59026786, compoundYield 97.1%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 21881883Oxolane--water (1/1)Solvent

Procedure

A mixture of 2-{5-[3-(2-Fluoro-4-iodo-phenylamino)-pyridin-4-yl]-[1,3,4]oxadiazol-2-ylamino}-propionic acid ethyl ester (45 mg, 0.09 mmol, 1.0 eq) and LiOH (5 mg, 0.18 mmol, 2 eq) in THF-H2O (1:1) (0.5 mL) was stirred at RT for 2 hr. The pH was adjusted to pH 5 with 1N HCl and the mixture was diluted with EtOAc, washed with brine, and dried over anhydrous MgSO4. Filtration and solvent removal resulted in a residue that was washed with ether to give rise to the desired product (41 mg). LC/MS (Method A) [5.04 min; 470(M+1)]

Workup

  1. washwashed with brine
  2. dry with materialdried over anhydrous MgSO4
  3. filtrationFiltration and solvent removal
  4. customresulted in a residue that
  5. washwas washed with ether

Sources & evidence

ORD record
ord-c8c089cb7dc34a07a06c85dc22f97272
Source dataset
uspto-grants-2011_12
Patent number
US08076486B2

Reaction notes

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