Lithium hydroxide, monohydrate → HCID 67994607, compound

HRID 2361379Notes

Reaction equation

HRID 2361379 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][N:7]([C:12]3[C:13]([CH3:40])=[C:14]([C:18]4[C:30]5[C:29]6[CH:28]=[CH:27][C:26]([O:31][CH2:32][CH2:33][O:34][CH3:35])=[CH:25][C:24]=6[NH:23][C:22]=5[C:21]([C:36]([O:38]C)=[O:37])=[N:20][N:19]=4)[CH:15]=[CH:16][CH:17]=3)[C:8]2=[O:11])=[CH:4][CH:3]=1.O.[OH-].[Li+]>C1COCC1.CO.O>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][N:7]([C:12]3[C:13]([CH3:40])=[C:14]([C:18]4[C:30]5[C:29]6[CH:28]=[CH:27][C:26]([O:31][CH2:32][CH2:33][O:34][CH3:35])=[CH:25][C:24]=6[NH:23][C:22]=5[C:21]([C:36]([OH:38])=[O:37])=[N:20][N:19]=4)[CH:15]=[CH:16][CH:17]=3)[C:8]2=[O:11])=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 67995325HCID 67995325, compound

Product 1

HCID 67994607HCID 67994607, compoundYield 42.3%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a yellow, homogeneous solution of methyl 1-(3-(6-chloro-1-oxoisoindolin-2-yl)-2-methylphenyl)-7-(2-methoxyethoxy)-5H-pyridazino [4,5-b]indole-4-carboxylate (0.05 g, 0.090 mmol) in THF (1.924 mL) and MeOH (0.641 mL) was added a solution of lithium hydroxide hydrate (0.015 g, 0.359 mmol) in water (0.5 mL). After 2.25 hr, the reaction was concentrated in vacuo, acidified with aqueous 1 N HCl to pH ˜4-5 by litmus paper. The precipitate was filtered and dried over Drierite to give the desired product (0.0206 g, 0.038 mmol, 42.3% yield) as a light tan solid.

Workup

  1. concentrationthe reaction was concentrated in vacuo
  2. filtrationThe precipitate was filtered
  3. dry with materialdried over Drierite

Sources & evidence

ORD record
ord-9eb15707eb654f799fd99828e7f9ca31
Source dataset
uspto-grants-2014_04
Patent number
US08685969B2

Reaction notes

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