Lithium Hydroxide → HCID 178525787, compound

HRID 931298Notes

Reaction equation

HRID 931298 reaction equation
[OH-].[Li+].[Cl:3][C:4]1[CH:5]=[N:6][N:7]([C:9]2([C:12]3[NH:31][C:15]4=[N:16][C:17]([N:20]5[CH2:25][CH2:24][CH2:23][C@@H:22]([C:26]([O:28]CC)=[O:27])[CH2:21]5)=[CH:18][CH:19]=[C:14]4[N:13]=3)[CH2:11][CH2:10]2)[CH:8]=1>O1CCCC1.O>[Cl:3][C:4]1[CH:5]=[N:6][N:7]([C:9]2([C:12]3[NH:31][C:15]4=[N:16][C:17]([N:20]5[CH2:25][CH2:24][CH2:23][C@@H:22]([C:26]([OH:28])=[O:27])[CH2:21]5)=[CH:18][CH:19]=[C:14]4[N:13]=3)[CH2:10][CH2:11]2)[CH:8]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 178472506(R)-ethyl 1-(2-(1-(4-chloro-1H-pyrazol-1-yl)cyclopropyl)-3H-imidazo[4,5-b]pyridin-5-yl)piperidine-3-carboxylate

Product 1

HCID 178525787HCID 178525787, compoundYield 67.1%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

Lithium hydroxide (27.6 mg, 1.1 mmol) was added to a solution of (R)-ethyl 1-(2-(1-(4-chloro-1H-pyrazol-1-yl)cyclopropyl)-3H-imidazo[4,5-b]pyridin-5-yl)piperidine-3-carboxylate (300 mg, 0.77 mmol) in tetrahydrofuran/water (1:1, 6 mL) at room temperature. The reaction mixture was stirred at room temperature for 3 h. The solvent was removed under reduced pressure. The residue was dissolved in water and the pH was adjusted to 6 using aqueous hydrogen chloride (1N). The mixture was extracted with ethyl acetate. The organics were dried over sodium sulfate, filtered and concentrated under reduced pressure to afford (R)-1-(2-(1-(4-chloro-1H-pyrazol-1-yl)cyclopropyl)-3H-imidazo[4,5-b]pyridin-5-yl)piperidine-3-carboxylic acid (200 mg). MS (ES+APCI) (M+H) 387.1; LCMS retention time 3.432 min (Method S1).

Workup

  1. customThe solvent was removed under reduced pressure
  2. dissolutionThe residue was dissolved in water
  3. extractionThe mixture was extracted with ethyl acetate
  4. dry with materialThe organics were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-090979bb47504e798107668a731b5ac9
Source dataset
uspto-grants-2016_03
Patent number
US09296745B2

Reaction notes

Loading…