HCID 66777585, compound → HCID 66778521, compound

HRID 2091418Notes

Reaction equation

HRID 2091418 reaction equation
[CH:1]1([CH:6]([NH:19][C:20]2[CH:25]=[CH:24][C:23]([C:26]([N:28]([CH3:36])[CH2:29][CH2:30][C:31]([O:33]CC)=[O:32])=[O:27])=[CH:22][CH:21]=2)[C:7]2[O:8][C:9]3[C:16]([F:17])=[CH:15][C:14]([F:18])=[CH:13][C:10]=3[C:11]=2[CH3:12])[CH2:5][CH2:4][CH2:3][CH2:2]1>C(O)C.O1CCCC1.[OH-].[Na+]>[CH:1]1([CH:6]([NH:19][C:20]2[CH:21]=[CH:22][C:23]([C:26]([N:28]([CH3:36])[CH2:29][CH2:30][C:31]([OH:33])=[O:32])=[O:27])=[CH:24][CH:25]=2)[C:7]2[O:8][C:9]3[C:16]([F:17])=[CH:15][C:14]([F:18])=[CH:13][C:10]=3[C:11]=2[CH3:12])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 1

HCID 66777585HCID 66777585, compound

Product 1

HCID 66778521HCID 66778521, compoundYield 82%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

Ethyl 3-{[(4-{[cyclopentyl(5,7-difluoro-3-methyl-1-benzofuran-2-yl)methyl]amino}phenyl)carbonyl](methyl)amino}propanoate (240 mg) synthesized in Example A207 was dissolved in ethanol (1.0 mL)-tetrahydrofuran (1.0 mL), 1N aqueous sodium hydroxide solution (0.96 mL) was added to the solution, and the mixture was stirred at room temperature for 30 min. The solvent was evaporated under reduced pressure, water (4 mL) was added to the residue, and the mixture was neutralized with 1N hydrochloric acid (0.96 mL) under ice-cooling, and stirred for 15 min. The resulting precipitate was collected by filtration, and dried to give the title compound (185 mg, 82%) as a colorless amorphous form.

Workup

  1. additionwas added to the solution
  2. customThe solvent was evaporated under reduced pressure, water (4 mL)
  3. additionwas added to the residue
  4. temperaturecooling
  5. stirringstirred for 15 min
  6. filtrationThe resulting precipitate was collected by filtration
  7. customdried

Sources & evidence

ORD record
ord-ef0d8e76ab8b49758e47325f694ece7e
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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