Hydrochloric Acid → HCID 12002220, compound

HRID 508102Notes

Reaction equation

HRID 508102 reaction equation
[C:1]1([C:7]2[CH:11]=[C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[N:9]([CH2:18][C:19]3[CH:41]=[CH:40][C:22]([CH2:23][NH:24][C:25]4[CH:30]=[C:29]([F:31])[C:28]([CH2:32][CH2:33][C:34]([O:36]CC)=[O:35])=[C:27]([F:39])[CH:26]=4)=[CH:21][C:20]=3[O:42][CH:43]([CH3:45])[CH3:44])[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].Cl>C(O)C.O1CCCC1>[C:1]1([C:7]2[CH:11]=[C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[N:9]([CH2:18][C:19]3[CH:41]=[CH:40][C:22]([CH2:23][NH:24][C:25]4[CH:30]=[C:29]([F:31])[C:28]([CH2:32][CH2:33][C:34]([OH:36])=[O:35])=[C:27]([F:39])[CH:26]=4)=[CH:21][C:20]=3[O:42][CH:43]([CH3:45])[CH3:44])[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 23157377HCID 23157377, compound

Product 1

HCID 12002220HCID 12002220, compoundYield 75.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of ethyl 3-[4-({4-[(3,5-diphenyl-1H-pyrazol-1-yl)methyl]-3-isopropoxybenzyl}amino)-2,6-difluorophenyl]propanoate (0.431 g, 0.710 mmol) in a mixture of ethanol (5 mL) and tetrahydrofuran (8 mL) was added 1 N sodium hydroxide (2.12 mL, 2.12 mmol) and the mixture was stirred at 60° C. for 1 hr. The reaction mixture was neutralized with 1 N hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was recrystallized from diethyl ether-hexane to give the title compound (0.310 g, yield 75%) as colorless crystals.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was recrystallized from diethyl ether-hexane

Sources & evidence

ORD record
ord-d0c7cc89c0244779b9ce4d4d19c6d1c2
Source dataset
uspto-grants-2010_08
Patent number
US07786165B2

Reaction notes

Loading…