Lithium Hydroxide → HCID 178525787, compound

HRID 931314Notes

Reaction equation

HRID 931314 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 89.8%

Reagents, catalysts & solvents 1

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

Procedure

Lithium hydroxide (182.4 mg, 4.32 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 (600 mg, 1.44 mmol) in tetrahydrofuran:water (1:1, 20 mL) at room temperature. The reaction mixture was stirred for 3 h. The solvent was removed under reduced pressure and the resulting residue was dissolved in water. The pH of the solution was adjusted to 2 using aqueous hydrochloric acid (1N), and the product was extracted with ethyl acetate. The organics were dried over sodium sulfate 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 (500 mg). The material was used for the next step without further purification. MS (ES+) (M+H) 387.3246.

Workup

  1. customThe solvent was removed under reduced pressure
  2. dissolutionthe resulting residue was dissolved in water
  3. extractionthe product was extracted with ethyl acetate
  4. dry with materialThe organics were dried over sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-526eeef679114509845ce629d725f81c
Source dataset
uspto-grants-2016_03
Patent number
US09296745B2

Reaction notes

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