Methanol → HCID 25161185, compound

HRID 1047928Notes

Reaction equation

HRID 1047928 reaction equation
C([O:3][C:4]([C:6]1([NH:15][C:16]([C:18]2[C:19]([N:24]([CH2:26][CH3:27])[CH3:25])=[N:20][CH:21]=[CH:22][CH:23]=2)=[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>[CH2:26]([N:24]([CH3:25])[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])=[CH:23][CH:22]=[CH:21][N:20]=1)[CH3:27]

Participants

5

Reactant 3

HCID 887MethanolHCID 312751,4-DioxaneHCID 59314240HCID 59314240, compound

Product 1

HCID 25161185HCID 25161185, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 100 mL round bottom flask which contains 2-{[2-(Ethyl-methyl-amino)-pyridine-3-carbonyl]-amino}-indan-2-carboxylic acid ethyl ester (337, 650 mg, 1.77 mmol) is charged with 1,4-dioxane (10 mL) and MeOH (10 mL). A stirring bar is added and stirring is initiated. After dissolution, water (5 mL) is added followed by the LiOH monohydrate (187 mg, 4.46 mmol). After 18 h, tlc analysis (silica, 50% EtOAc/heptanes) indicates that the starting material is completely consumed. Amberlyst highly acidic exchange resin (1 g) is added to the reaction vial. The reaction is capped and allowed to stir at ambient temperature. After 18 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 under reduced pressure. This process is repeated 1 time. Pumping to constant weight gives beige solid (0.58 g, 97%).

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 (1 g) is added to the reaction vial
  6. customThe reaction is capped
  7. stirringto stir at ambient temperature
  8. waitAfter 18 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 under reduced pressure

Sources & evidence

ORD record
ord-5e8e9337d9434b90b017d82a91fc35a2
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

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