Tetrahydrofuran → HCID 117840315, compound

HRID 1520300Notes

Reaction equation

HRID 1520300 reaction equation
[CH3:1][CH:2]([CH3:31])[CH:3]([NH:20][C:21]1[CH:30]=[CH:29][C:24]([C:25]([O:27]C)=[O:26])=[CH:23][CH:22]=1)[C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH:18]=[C:17]3[C:12]([CH2:13][CH2:14][CH2:15][CH2:16]3)=[N:11]2)=[CH:6][C:5]=1[CH3:19].C1COCC1.[OH-].[Na+]>CO>[CH3:1][CH:2]([CH3:31])[CH:3]([NH:20][C:21]1[CH:30]=[CH:29][C:24]([C:25]([OH:27])=[O:26])=[CH:23][CH:22]=1)[C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH:18]=[C:17]3[C:12]([CH2:13][CH2:14][CH2:15][CH2:16]3)=[N:11]2)=[CH:6][C:5]=1[CH3:19]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 117840578HCID 117840578, compound

Product 1

HCID 117840315HCID 117840315, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a mixture of methyl 4-((2-methyl-1-(2-methyl-4-(4,5,6,7-tetrahydro-2H-indazol-2-yl)phenyl)propyl)amino)benzoate (137.3 mg), THF (0.6 mL) and methanol (0.6 mL) was added 1M aqueous sodium hydroxide solution (0.658 mL), and the mixture was stirred at 50° C. overnight. The solvent was evaporated under reduced pressure, the resulting mixture was neutralized with 1M hydrochloric acid (0.658 mL), and extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give the title compound as a crudely purified product. This compound was used in step D without further purification.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-a1a2d495ad7c418a9efda28ff223157a
Source dataset
uspto-grants-2015_07
Patent number
US09073864B2

Reaction notes

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