Lithium hydroxide, monohydrate → HCID 58497439, compound

HRID 2175191Notes

Reaction equation

HRID 2175191 reaction equation
C([O:3][C:4](=[O:32])[CH:5]([CH2:9][N:10]1[C:14]2=[N:15][CH:16]=[CH:17][CH:18]=[C:13]2[N:12]([CH2:19][C:20]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][C:27]=3[CH3:29])[N:22]([CH3:30])[CH:21]=2)[C:11]1=[O:31])[CH2:6][CH2:7][CH3:8])C.O.[OH-].[Li+]>O1CCOCC1.O>[CH3:30][N:22]1[C:23]2[C:28](=[C:27]([CH3:29])[CH:26]=[CH:25][CH:24]=2)[C:20]([CH2:19][N:12]2[C:13]3[C:14](=[N:15][CH:16]=[CH:17][CH:18]=3)[N:10]([CH2:9][CH:5]([CH2:6][CH2:7][CH3:8])[C:4]([OH:32])=[O:3])[C:11]2=[O:31])=[CH:21]1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 58497412HCID 58497412, compound

Product 1

HCID 58497439HCID 58497439, compoundYield 31%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of 2-[1-(1,4-dimethyl-1H-indol-3-ylmethyl)-2-oxo-1,2-dihydro-imidazo[4,5-b]pyridin-3-ylmethyl]-pentanoic acid ethyl ester (85 mg, 0.20 mmol) in dioxane (5 ml) and water (1.5 ml) was added lithium hydroxide monohydrate (41 mg, 0.98 mmol) at room temperature. After stirring overnight the reaction appeared complete. The reaction was concentrated to low volume and diluted with water (˜20 ml). Acidified using HOAc and collected the resulting precipitate via filtration. The product was suspended in 2 ml of 1:1 MeOH/acetonitrile, filtered and washed with acetonitrile. The solid was dried on house vacuum to give 25 mg (31%) of the title compound. LCMS, M++1, m/z: 407.91.

Workup

  1. concentrationThe reaction was concentrated to low volume
  2. additiondiluted with water (˜20 ml)
  3. customcollected the resulting precipitate
  4. filtrationvia filtration
  5. filtrationfiltered
  6. washwashed with acetonitrile
  7. customThe solid was dried on house vacuum

Sources & evidence

ORD record
ord-243a257d6d9d4b2eaa9c1c1068758ed3
Source dataset
uspto-grants-2015_06
Patent number
US09062056B2

Reaction notes

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