Methanol → HCID 59314266, compound

HRID 1047941Notes

Reaction equation

HRID 1047941 reaction equation
C([O:3][C:4]([C:6]1([NH:15][C:16]([C:18]2[C:23]([N:24]3[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]3)=[CH:22][CH:21]=[CH:20][N:19]=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>[N:24]1([C:23]2[C:18]([C:16]([NH:15][C:6]3([C:4]([OH:5])=[O:3])[CH2:14][C:13]4[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=4)[CH2:7]3)=[O:17])=[N:19][CH:20]=[CH:21][CH:22]=2)[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1

Participants

5

Reactant 3

HCID 887MethanolHCID 312751,4-DioxaneHCID 59314200HCID 59314200, compound

Product 1

HCID 59314266HCID 59314266, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 100 mL round bottom flask which contains 2-[(3,4,5,6-Tetrahydro-2H-[1,3′]bipyridinyl-2′-carbonyl)-amino]-indan-2-carboxylic acid ethyl ester (360, 370 mg, 0.94 mmol) is charged with 1,4-dioxane (4 mL) and MeOH (4 mL). A stirring bar is added and stirring is initiated. After dissolution, water (2 mL) is added followed by LiOH monohydrate (100 mg, 2.38 mmol). After 38 h, tlc analysis (silica, 50% EtOAc/heptanes) indicates that the starting material has been 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 4 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 (0.29, 84%).

Workup

  1. customA 100 mL round bottom flask which contains
  2. additionA stirring bar is added
  3. additionis added
  4. customhas been 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 4 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
  12. customprovides white solid (0.29, 84%)

Sources & evidence

ORD record
ord-2f4caf5f93cc4cc6b963464493a2549c
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

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