Methanol → HCID 59314114, compound

HRID 1047932Notes

Reaction equation

HRID 1047932 reaction equation
C([O:3][C:4]([C:6]1([NH:15][C:16]([C:18]2[C:19]([N:26]([CH2:28][CH3:29])[CH3:27])=[N:20][C:21]([CH3:25])=[CH:22][C:23]=2[CH3:24])=[O:17])[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7]1)=[O:5])C.O1CCOCC1.CO>O>[CH2:28]([N:26]([CH3:27])[C:19]1[C:18]([C:16]([NH:15][C:6]2([C:4]([OH:5])=[O:3])[CH2:14][C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH2:7]2)=[O:17])=[C:23]([CH3:24])[CH:22]=[C:21]([CH3:25])[N:20]=1)[CH3:29]

Participants

5

Reactant 3

HCID 887MethanolHCID 312751,4-DioxaneHCID 59314160HCID 59314160, compound

Product 1

HCID 59314114HCID 59314114, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 100 mL round bottom flask which contains 2-{[2-(ethyl-methyl-amino)-4,6-dimethyl-pyridine-3-carbonyl]-amino}-indan-2-carboxylic acid ethyl ester (348, 260 mg, 0.66 mmol) is charged with 1,4-dioxane (3 mL) and MeOH (3 mL). A stirring bar is added and stirring is initiated. After dissolution, water (1.5 mL) is added followed by the LiOH monohydrate (70 mg, 1.66 mmol). After 18 h, tlc analysis (silica, 50% EtOAc/heptanes) indicates that the starting material is completely consumed. Amberlyst highly acidic exchange resin (0.5 g) is added to the reaction vial. The reaction is capped and allowed to stir at ambient temperature. After 38 h, the contents of the flask are filtered through a pad of Celite. The solvent is removed from the filtrate. The residue is reconstituted with iPrOH/toluene (20+20 mL) and the solvent is removed. This process is repeated 1 time. Pumping to constant weight provides white solid (0.18 g, 75%).

Workup

  1. customA 100 mL round bottom flask which contains
  2. additionA stirring bar is added
  3. additionis added
  4. customis completely consumed
  5. additionAmberlyst highly acidic exchange resin (0.5 g) is added to the reaction vial
  6. customThe reaction is capped
  7. stirringto stir at ambient temperature
  8. waitAfter 38 h
  9. filtrationthe contents of the flask are filtered through a pad of Celite
  10. customThe solvent is removed from the filtrate
  11. customthe solvent is removed

Sources & evidence

ORD record
ord-f8138587feee4191adc438e90f39c4f5
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

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