Methanol → 2-(Isoquinolin-5-ylcarbamoyl)-indan-2-carboxylic Acid

HRID 1047915Notes

Reaction equation

HRID 1047915 reaction equation
C([O:3][C:4]([C:6]1([C:15](=[O:27])[NH:16][C:17]2[CH:26]=[CH:25][CH:24]=[C:23]3[C:18]=2[CH:19]=[CH:20][N:21]=[CH:22]3)[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>CO.C(Cl)Cl>[CH:22]1[C:23]2[C:18](=[C:17]([NH:16][C:15]([C:6]3([C:4]([OH:5])=[O:3])[CH2:7][C:8]4[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=4)[CH2:14]3)=[O:27])[CH:26]=[CH:25][CH:24]=2)[CH:19]=[CH:20][N:21]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 312751,4-DioxaneHCID 59314243HCID 59314243, compound

Product 1

HCID 593140872-(Isoquinolin-5-ylcarbamoyl)-indan-2-carboxylic AcidYield 86%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

A 30 mL reaction vial is charged with 2-(isoquinolin-5-ylcarbamoyl)-indan-2-carboxylic acid ethyl ester (320, 354 mg, 0.98 mmol) is charged with 1,4-dioxane (6 mL) and MeOH (6 mL). A stirring bar is added and stirring is initiated. After dissolution, water (3 mL) is added followed by the LiOH monohydrate (104 mg, 252 mmol). After 20 h, tlc analysis (silica, 10% MeOH/DCM) 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 64 h, the contents of the flask are filtered through a pad of Celite. The solvent is removed from the filtrate by pumping to constant weight to give 0.29 g of off white solid. This material is triturated with DCM (15 mL). The solids are collected by suction filtration and washed with DCM (20 mL). Suction drying provides off white solid (280 mg, 86%).

Workup

  1. customA 30 mL reaction
  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 64 h
  9. filtrationthe contents of the flask are filtered through a pad of Celite
  10. customThe solvent is removed from the filtrate
  11. customto give 0.29 g of off white solid
  12. customThis material is triturated with DCM (15 mL)
  13. filtrationThe solids are collected by suction filtration
  14. washwashed with DCM (20 mL)
  15. customSuction drying

Sources & evidence

ORD record
ord-cf11f05bdab0465482d707fca75fe9d1
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

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