Tetrahydrofuran → HCID 66777998, compound

HRID 2091422Notes

Reaction equation

HRID 2091422 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[CH:7]=[CH:8][C:9]3[O:13][C:12]([CH:14]([NH:18][C:19]4[CH:20]=[CH:21][C:22]([C:25]([O:27]C)=[O:26])=[N:23][CH:24]=4)[CH:15]([CH3:17])[CH3:16])=[C:11]([CH3:29])[C:10]=3[CH:30]=2)[CH2:3][CH2:2]1.O1CCCC1.[OH-].[Na+]>C(O)C>[CH:1]1([CH2:4][O:5][C:6]2[CH:7]=[CH:8][C:9]3[O:13][C:12]([CH:14]([NH:18][C:19]4[CH:20]=[CH:21][C:22]([C:25]([OH:27])=[O:26])=[N:23][CH:24]=4)[CH:15]([CH3:17])[CH3:16])=[C:11]([CH3:29])[C:10]=3[CH:30]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 66778895HCID 66778895, compound

Product 1

HCID 66777998HCID 66777998, compoundYield 81.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of methyl 5-({1-[5-(cyclopropylmethoxy)-3-methyl-1-benzofuran-2-yl]-2-methylpropyl}amino)pyridine-2-carboxylate (410 mg) synthesized above, tetrahydrofuran (2.0 mL) and ethanol (2.0 mL) was added 1N aqueous sodium hydroxide solution (2.0 mL), and the mixture was stirred with heating under reflux for 14 hr. The reaction mixture was concentrated under reduced pressure, water (4 mL) was added to the residue, 1N hydrochloric acid (2 mL) was added under ice-cooling, and the mixture was stirred for 20 min. The resulting precipitate was collected by filtration, and dried to give the title compound (323 mg, 80%) as a colorless solid.

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for 14 hr
  3. concentrationThe reaction mixture was concentrated under reduced pressure, water (4 mL)
  4. additionwas added to the residue, 1N hydrochloric acid (2 mL)
  5. additionwas added under ice-
  6. temperaturecooling
  7. stirringthe mixture was stirred for 20 min
  8. filtrationThe resulting precipitate was collected by filtration
  9. customdried

Sources & evidence

ORD record
ord-34f18a9fa5974cbd82be5f9312add772
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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