Pyridine → HCID 11463284, compound

HRID 1357237Notes

Reaction equation

HRID 1357237 reaction equation
[C:1]1([N:7]2[C:11]([CH2:12][CH2:13][CH3:14])=[C:10]([C:15](Cl)=[O:16])[CH:9]=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:18][CH2:19][C:20]1[CH:21]=[C:22]2[C:27](=[CH:28][CH:29]=1)[CH:26]=[C:25]([OH:30])[CH:24]=[CH:23]2.N1C=CC=CC=1>C(Cl)Cl>[OH:30][C:25]1[CH:26]=[C:27]2[C:22](=[CH:23][CH:24]=1)[CH:21]=[C:20]([CH2:19][NH:18][C:15]([C:10]1[CH:9]=[N:8][N:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[C:11]=1[CH2:12][CH2:13][CH3:14])=[O:16])[CH:29]=[CH:28]2

Participants

5

Reactant 3

HCID 1049PyridineHCID 37757171-Phenyl-5-propyl-1H-pyrazole-4-carbonyl chlorideHCID 118161426-(Aminomethyl)-2-naphthol

Product 1

HCID 11463284HCID 11463284, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 1-phenyl-5-propyl-1H-pyrazole-4-carbonyl chloride (2.0 g, 8 mmol) in 20 mL of methylene chloride was added dropwise under nitrogen to a mixture of 6-aminomethyl-naphthalen-2-ol (1.63 g, 9.42 mmol), prepared in step 1 of Example 8, and 75 mL of anhydrous pyridine. The reaction stirred at room temperature for 17 h (overnight). The reaction was diluted with methylene chloride and extracted with 1N HCl. The aqueous layer was separated and extracted with methylene chloride. The organic extracts were combined, dried (MgSO4) and the solvent removed under reduced pressure to give a brown solid. The solid was recrystallized from ethyl acetate and then again from isopropanol. The crystals were collected by filtration and dried under reduced pressure to give 1-phenyl-5-propyl-1H-pyrazole-4-carboxylic acid (6-hydroxy-naphthalen-2-ylmethyl)-amide (0.767 g, 25%) as a tan solid, mp 189-190° C.

Workup

  1. extractionextracted with 1N HCl
  2. customThe aqueous layer was separated
  3. extractionextracted with methylene chloride
  4. dry with materialdried (MgSO4)
  5. customthe solvent removed under reduced pressure
  6. customto give a brown solid
  7. customThe solid was recrystallized from ethyl acetate
  8. filtrationThe crystals were collected by filtration
  9. customdried under reduced pressure

Sources & evidence

ORD record
ord-805a7ba6f22c47da8bc8d530b9409f1f
Source dataset
uspto-grants-2003_07
Patent number
US06589970B2

Reaction notes

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