Hydrochloric Acid → HCID 10181928, compound

HRID 1357225Notes

Reaction equation

HRID 1357225 reaction equation
[OH-].[Na+].C[O:4][C:5](=[O:36])[CH2:6][O:7][C:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([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]=2)[CH:9]=1.O.Cl>CO>[C:30]1([N:25]2[C:26]([CH2:27][CH2:28][CH3:29])=[C:22]([C:20]([NH:19][CH2:18][C:13]3[CH:14]=[C:15]4[C:10](=[CH:11][CH:12]=3)[CH:9]=[C:8]([O:7][CH2:6][C:5]([OH:36])=[O:4])[CH:17]=[CH:16]4)=[O:21])[CH:23]=[N:24]2)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 69137586HCID 69137586, compound

Product 1

HCID 10181928HCID 10181928, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1 N NaOH (431 μL, 0.431 mmol) was added under nitrogen to a solution at room temperature of (6-{[(1-phenyl-5-propyl-1H-pyrazole-4-carbonyl)-amino]-methyl}-naphthalen-2-yloxy)-acetic acid methyl ester (170 mg, 0.359 mmol), prepared in the previous step, in 25 mL of MeOH plus 10 mL of water. After the addition the reaction was stirred at room temperature for 18 h (overnight). The reaction was acidified with 1 N HCl and then concentrated under reduced pressure to remove the MeOH. The solid present was collected by filtration and dried under reduced pressure to give the title compound (146 mg, 92%) as an off-white solid, mp 175-177° C.

Workup

  1. additionAfter the addition the reaction
  2. concentrationconcentrated under reduced pressure
  3. customto remove the MeOH
  4. filtrationThe solid present was collected by filtration
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-47bc2b8ef0ae4f9c98c279ca1bb31f46
Source dataset
uspto-grants-2003_07
Patent number
US06589970B2

Reaction notes

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