Lithium Hydroxide → HCID 118590363, compound

HRID 1054474Notes

Reaction equation

HRID 1054474 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C@@H:9]1[CH2:13][CH2:12][CH2:11][N:10]1[C:14]1[CH:15]=[CH:16][C:17]2[N:18]([C:20]([C:23]([NH:25][CH2:26][C:27]([O:29]CC)=[O:28])=[O:24])=[CH:21][N:22]=2)[CH:19]=1.[Li+].[OH-]>C(O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C@@H:9]1[CH2:13][CH2:12][CH2:11][N:10]1[C:14]1[CH:15]=[CH:16][C:17]2[N:18]([C:20]([C:23]([NH:25][CH2:26][C:27]([OH:29])=[O:28])=[O:24])=[CH:21][N:22]=2)[CH:19]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 118590287HCID 118590287, compound

Product 1

HCID 118590363HCID 118590363, compoundYield 48.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of (S)-ethyl 2-(6-(2-(2,5-difluorophenyl)pyrrolidin-1-yl)imidazo[1,2-a]pyridine-3-carboxamido)acetate (Example-18; Isomer-II) (0.08 g, 0.18 mmol) in ethanol (10 mL) was added 1M LiOH solution at 20° C. then stirred for 1 h RT. After completion of reaction solvent was remove under reduced pressure then residue was dissolved in water and washed with diethylether and water layer was acidified with 2N HCl (pH˜2) and solid was filter to afford pure (S)-2-(6(2(2,5difluorophenyl)pyrrolidin-1-yl)imidazo[1,2-a]pyridine-3-carboxamido)acetic acid (Isomer-II) (0.035 g, 47.29% Yield). MS (ESI): m/z 401.3 (M+H); 1H NMR (300 MHz, DMSO-d6) δ 12.66-12.60 (1H, bs), 8.75-8.72 (2H, m), 8.27 (1H, s), 7.59-7.55 (1H, d J=12 Hz), 7.35-7.28 (1H, m), 7.16-7.10 (1H, m), 7.00-6.93 (2H, m), 5.00-4.98 (1H, d J=6 Hz), 3.93-3.91 (2H, d J=6 Hz), 3.79-3.74 (1H, m), 2.03-1.87 (3H, m) ppm.

Workup

  1. customAfter completion of reaction solvent
  2. customwas remove under reduced pressure
  3. dissolutionresidue was dissolved in water
  4. washwashed with diethylether and water layer
  5. filtrationwas filter

Sources & evidence

ORD record
ord-c810962e35f34478a1b0d2a9971fdbe0
Source dataset
uspto-grants-2016_07
Patent number
US09394305B2

Reaction notes

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