Lithium Hydroxide → HCID 59026822, compound

HRID 658384Notes

Reaction equation

HRID 658384 reaction equation
C[O:2][C:3](=[O:26])[CH2:4][NH:5][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.[Li+].[OH-]>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][C:6]([NH:5][CH2:4][C:3]([OH:26])=[O:2])=[N:10][N:9]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 59026775HCID 59026775, compound

Product 1

HCID 59026822HCID 59026822, compoundYield 74.5%

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]oxadiazol-2-ylamino}-acetic acid methyl ester (262 mg, 0.56 mmol, 1 eq) in THF-H2O (1:1) (2 mL) LiOH (27 mg, 1.12 mmol, 2 eq) was added. The reaction mixture was stirred at RT for 2 hrs. The solvent was removed partially and more water was added. The mixture was washed with ether and the pH of the aqueous layer was adjusted to 3 with 1N HCl. A solid precipitated and filtered to afford the desired product (190 mg). LC/MS (Method A) [4.83 min; 456(M+1)]

Workup

  1. customThe solvent was removed partially
  2. additionmore water was added
  3. washThe mixture was washed with ether
  4. customA solid precipitated
  5. filtrationfiltered

Sources & evidence

ORD record
ord-917fa44272a04471ba4d9e51fb0b0f34
Source dataset
uspto-grants-2011_12
Patent number
US08076486B2

Reaction notes

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