Lithium Hydroxide → HCID 178492745, compound

HRID 931225Notes

Reaction equation

HRID 931225 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]=[C:12]([C:14]2[NH:35][C:17]3=[N:18][C:19]([N:22]4[CH2:27][CH2:26][CH2:25][C@@H:24]([C:28]([N:30]5[CH2:34][CH2:33][CH2:32][CH2:31]5)=[O:29])[CH2:23]4)=[CH:20][CH:21]=[C:16]3[N:15]=2)[N:13]=1)[C:6]([O:8]CC)=[O:7].[OH-].[Li+]>O1CCCC1.CO.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]=[C:12]([C:14]2[NH:35][C:17]3=[N:18][C:19]([N:22]4[CH2:27][CH2:26][CH2:25][C@@H:24]([C:28]([N:30]5[CH2:34][CH2:33][CH2:32][CH2:31]5)=[O:29])[CH2:23]4)=[CH:20][CH:21]=[C:16]3[N:15]=2)[N:13]=1)[C:6]([OH:8])=[O:7]

Participants

6

Reactant 2

HCID 3939Lithium HydroxideHCID 178469330HCID 178469330, compound

Product 1

HCID 178492745HCID 178492745, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (R)-ethyl 2-methoxy-6-(5-(3-(pyrrolidine-1-carbonyl)piperidin-1-yl)-3H-imidazo[4,5-b]pyridin-2-yl)isonicotinate (Example 96, 50 mg, 0.1 mmol) in tetrahydrofuran (1.0 mL) was added a solution of lithium hydroxide (14.9 mg, 0.6 mmol) in methanol (1.0 mL) and water (1.0 mL). The resulting suspension was stirred at room temperature for 2 h. The mixture was concentrated under reduced pressure. To the residue was added a saturated solution of ammonium chloride in water (10 mL). The pH of the mixture was adjusted to 3 using aqueous hydrochloric acid (1N). The mixture was extracted with ethyl acetate (20 mL×3). The organics were combined, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified via HPLC to afford the title compound. MS (ESI+) (M+H) 451.1; HPLC retention time 2.21 min (Method A).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. additionTo the residue was added a saturated solution of ammonium chloride in water (10 mL)
  3. extractionThe mixture was extracted with ethyl acetate (20 mL×3)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified via HPLC

Sources & evidence

ORD record
ord-01a54723413a4b69aa78712642540106
Source dataset
uspto-grants-2016_03
Patent number
US09296745B2

Reaction notes

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