HCID 66777839, compound → HCID 66779319, compound

HRID 2091421Notes

Reaction equation

HRID 2091421 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[N:24]=[CH:23][C:22]([C:25]([N:27]([CH3:35])[CH2:28][CH2:29][C:30]([O:32]CC)=[O:31])=[O:26])=[CH:21][CH:20]=4)[CH:15]([CH3:17])[CH3:16])=[C:11]([CH3:36])[C:10]=3[CH:37]=2)[CH2:3][CH2:2]1>C(O)C.O1CCCC1.[OH-].[Na+]>[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[N:24]=[CH:23][C:22]([C:25]([N:27]([CH3:35])[CH2:28][CH2:29][C:30]([OH:32])=[O:31])=[O:26])=[CH:21][CH:20]=4)[CH:15]([CH3:17])[CH3:16])=[C:11]([CH3:36])[C:10]=3[CH:37]=2)[CH2:2][CH2:3]1

Participants

5

Reactant 1

HCID 66777839HCID 66777839, compound

Product 1

HCID 66779319HCID 66779319, compoundYield 81.5%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

Ethyl 3-[{[6-({1-[5-(cyclopropylmethoxy)-3-methyl-1-benzofuran-2-yl]-2-methylpropyl}amino)pyridin-3-yl]carbonyl}(methyl)amino]propanoate (100 mg) synthesized in Example A210 was dissolved in ethanol (0.5 mL)-tetrahydrofuran (0.5 mL), 1N aqueous sodium hydroxide solution (0.4 mL) was added to the solution, and the mixture was stirred at room temperature for 2 hr. The solvent was evaporated under reduced pressure, water (0.5 mL) was added to the residue, and the mixture was neutralized with 1N hydrochloric acid (0.4 mL) 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 (77 mg, 80%) as a colorless solid.

Workup

  1. additionwas added to the solution
  2. customThe solvent was evaporated under reduced pressure, water (0.5 mL)
  3. additionwas added to the residue
  4. temperaturecooling
  5. stirringthe mixture was stirred for 20 min
  6. filtrationThe resulting precipitate was collected by filtration
  7. customdried

Sources & evidence

ORD record
ord-6bbaedfc8d0c40e78d3a7a486c5125da
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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