Lithium Hydroxide → HCID 24958698, compound

HRID 1873599Notes

Reaction equation

HRID 1873599 reaction equation
C([O:4][CH2:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[C:19]([C:20]#[N:21])=[C:18]([S:22][CH2:23][C:24]3[N:25]=[C:26]([C:29]4[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=4)[S:27][CH:28]=3)[N:17]=[C:16]([NH2:36])[C:15]=2[C:37]#[N:38])[CH2:10][CH2:9]1)=[O:7])(=O)C.[OH-].[Li+]>O1CCOCC1.O>[NH2:36][C:16]1[C:15]([C:37]#[N:38])=[C:14]([CH:11]2[CH2:12][CH2:13][N:8]([C:6](=[O:7])[CH2:5][OH:4])[CH2:9][CH2:10]2)[C:19]([C:20]#[N:21])=[C:18]([S:22][CH2:23][C:24]2[N:25]=[C:26]([C:29]3[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=3)[S:27][CH:28]=2)[N:17]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 687021312-{4-[2-Amino-6-({[2-(4-chlorophenyl)-1,3-thiazol-4-yl]methyl}thio)-3,5-dicyanopyridin-4-yl]-piperidin-1-yl}-2-oxoethyl acetate

Product 1

HCID 24958698HCID 24958698, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

29 mg (0.05 mmol) of the compound from Example 25A are dissolved in a mixture of 1.5 ml of dioxane and 0.8 ml of water, and 2.4 mg (0.10 mmol) of lithium hydroxide are added. The reaction mixture is stirred at RT for two hours. After removal of the solvent on a rotary evaporator the residue is purified by preparative HPLC (column: YMC GEL ODS-AQ S-5, 15 μm; mobile phase gradient: acetonitrile/water 10:90→95:5).

Workup

  1. additionare added
  2. customAfter removal of the solvent
  3. customon a rotary evaporator the residue
  4. customis purified by preparative HPLC (column: YMC GEL ODS-AQ S-5, 15 μm; mobile phase gradient: acetonitrile/water 10:90→95:5)

Sources & evidence

ORD record
ord-32c81903e6274b8a9fe9aaa4726bab27
Source dataset
uspto-grants-2012_11
Patent number
US08304412B2

Reaction notes

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