Hydrochloric Acid → HCID 11236744, compound

HRID 493474Notes

Reaction equation

HRID 493474 reaction equation
C[O:2][C:3](=[O:36])[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:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[C:26]=3[CH2:27][CH2:28][CH3:29])=[O:21])=[CH:14][CH:13]=2)=[CH:8][CH:7]=1.[OH-].[Na+].Cl>C1COCC1.O>[C:30]1([N:25]2[C:26]([CH2:27][CH2:28][CH3:29])=[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:36])=[O:2])=[CH:11][CH:10]=4)=[CH:13][CH:14]=3)=[O:21])[CH:23]=[N:24]2)[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 90766598HCID 90766598, compound

Product 1

HCID 11236744HCID 11236744, compoundYield 88.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl({4′-[({[1-phenyl-5-propyl-1H-pyrazol-4-yl]carbonyl}amino)methyl][1,1′-biphenyl]-4-yl}oxy)acetate (250 mg, 0.517 mmol), prepared in the previous step, and 1 N NaOH (620 μL, 0.620 mmol) in 40 mL of THF and 20 mL of water was stirred at room temperature for 19 h (overnight). The reaction was acidified by the addition of 620 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 (214 mg, 87%) as a white solid, mp 190-192° C. Elemental Analysis for C28H27N3O4+0.43 H2O. Calc'd: C, 70.46; H, 5.88; N, 8.80. Found: C, 70.37; H, 5.98; N, 8.44

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-9f95898f34724141828ff8413d104941
Source dataset
uspto-grants-2009_05
Patent number
US07534894B2

Reaction notes

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