Hydrochloric Acid → HCID 11386393, compound

HRID 493473Notes

Reaction equation

HRID 493473 reaction equation
C[O:2][C:3](=[O:37])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][C:15]([CH2:18][NH:19][C:20]([C:22]3[CH:23]=[N:24][N:25]([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)[C:26]=3[C:27]([F:30])([F:29])[F:28])=[O:21])=[CH:14][CH:13]=2)=[CH:8][CH:7]=1.[OH-].[Na+].Cl>C1COCC1.O>[C:31]1([N:25]2[C:26]([C:27]([F:30])([F:28])[F:29])=[C:22]([C:20]([NH:19][CH2:18][C:15]3[CH:16]=[CH:17][C:12]([C:9]4[CH:8]=[CH:7][C:6]([O:5][CH2:4][C:3]([OH:37])=[O:2])=[CH:11][CH:10]=4)=[CH:13][CH:14]=3)=[O:21])[CH:23]=[N:24]2)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 131727446HCID 131727446, compound

Product 1

HCID 11386393HCID 11386393, compoundYield 90.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl({4′-[({[1-phenyl-5-(trifluoromethyl)-1H-pyrazol-4-yl]carbonyl}amino)methyl][1,1′-biphenyl]-4-yl}oxy)acetate (284 mg, 0.557 mmol), prepared in the previous step, and 1 N NaOH (668 μL, 0.668 mmol) in 20 mL of THF and 10 mL of water was stirred at room temperature for 20 h (overnight). The reaction was acidified by the addition of 668 μL of 1 N HCl and then concentrated under reduced pressure to remove the THF. The solid that formed was collected by filtration and dried under reduced pressure to give the title compound (249 mg, 89%) as a white solid, MS (APCI) m/z 496 [M+H]+. Elemental Analysis for C26H20F3N3O4+0.38 H2O. Calc'd: C, 62.17; H, 4.17; N, 8.37Found: C, 61.91; H, 4.08; N, 8.00

Workup

  1. concentrationconcentrated under reduced pressure
  2. customto remove the THF
  3. customThe solid that formed
  4. filtrationwas collected by filtration
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-6fba6ee67bba4e0c87d4946c5a409952
Source dataset
uspto-grants-2009_05
Patent number
US07534894B2

Reaction notes

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