Methanol → HCID 59314081, compound

HRID 1047938Notes

Reaction equation

HRID 1047938 reaction equation
C([O:3][C:4]([C:6]1([NH:15][C:16]([C:18]2[CH:23]=[CH:22][N:21]=[CH:20][C:19]=2[N:24]([CH:26]([CH3:28])[CH3:27])[CH3:25])=[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>[CH:26]([N:24]([CH3:25])[C:19]1[CH:20]=[N:21][CH:22]=[CH:23][C:18]=1[C:16]([NH:15][C:6]1([C:4]([OH:5])=[O:3])[CH2:7][C:8]2[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:14]1)=[O:17])([CH3:28])[CH3:27]

Participants

5

Reactant 3

HCID 887MethanolHCID 312751,4-DioxaneHCID 59314293HCID 59314293, compound

Product 1

HCID 59314081HCID 59314081, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-{[3-(Isopropyl-methyl-amino)-pyridine-4′-carbonyl]-amino}-indan-2-carboxylic acid ethyl ester 357, 270 mg, 0.71 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 (75 mg, 1.94 mmol). After 4 days, 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 3 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 (0.22 g, 88%).

Workup

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

Sources & evidence

ORD record
ord-1aa09a2f13534e0690bb58ee1e09f0eb
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

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