Methanol → HCID 25161179, compound

HRID 1047929Notes

Reaction equation

HRID 1047929 reaction equation
C([O:3][C:4]([C:6]1([NH:15][C:16]([C:18]2[C:19]([NH:24][CH2:25][CH2:26][CH:27]=C)=[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.O1CCOC[CH2:30]1.CO>O>[CH2:25]([N:24]([CH3:30])[C:19]1[C:18]([C:16]([NH:15][C:6]2([C:4]([OH:3])=[O:5])[CH2:7][C:8]3[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=3)[CH2:14]2)=[O:17])=[CH:23][CH:22]=[CH:21][N:20]=1)[CH:26]=[CH2:27]

Participants

5

Reactant 3

HCID 887MethanolHCID 312751,4-DioxaneHCID 68590346HCID 68590346, compound

Product 1

HCID 25161179HCID 25161179, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 100 mL round bottom flask which contains 2-{[2-(allyl-methyl-amino)-pyridine-3-carbonyl]-amino}-indan-2-carboxylic acid ethyl ester (339, 280 mg, 0.74 mmol) is charged with 1,4-dioxane (2 mL) and MeOH (2 mL). A stirring bar is added and stirring is initiated. After dissolution, water (1 mL) is added followed by the LiOH monohydrate (78 mg, 1.86 mmol). After 38 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 15 days, 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 (0.26 g, 100%).

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 15 days
  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-706aa14ffd07436bb27def8da9f17651
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

Loading…