Lithium Hydroxide → HCID 24958702, compound

HRID 1873601Notes

Reaction equation

HRID 1873601 reaction equation
C([O:4][CH2:5][CH2:6][CH2:7][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)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]([CH2:7][CH2:6][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 Hydroxide2×HCID 24958699HCID 24958699, compound

Product 1

HCID 24958702HCID 24958702, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

65 mg (0.12 mmol) of the compound from Example 10 are initially charged in a mixture of 3.5 ml of dioxane and 1.7 ml of water, and 11 mg of lithium hydroxide are added. The mixture is initially stirred at RT for 8 h. Another 22 mg of lithium hydroxide are then added, and the mixture is stirred at RT for a further 16 h. The solvent is then removed on a rotary evaporator. The residue is taken up in 10 ml ethyl acetate and washed once with 3 ml of saturated aqueous sodium bicarbonate solution. The mixture is dried over magnesium sulfate. After removal of the solvent on a rotary evaporator the residue is purified chromatographically on silica gel 60 (mobile phase: gradient dichloromethane/ethanol 50:1→10:1).

Workup

  1. additionare added
  2. stirringthe mixture is stirred at RT for a further 16 h
  3. customThe solvent is then removed on a rotary evaporator
  4. washwashed once with 3 ml of saturated aqueous sodium bicarbonate solution
  5. dry with materialThe mixture is dried over magnesium sulfate
  6. customAfter removal of the solvent
  7. customon a rotary evaporator the residue
  8. customis purified chromatographically on silica gel 60 (mobile phase: gradient dichloromethane/ethanol 50:1→10:1)

Sources & evidence

ORD record
ord-c47e1d00f7f34ed48473ced9df1808ef
Source dataset
uspto-grants-2012_11
Patent number
US08304412B2

Reaction notes

Loading…