Hydrochloric Acid → HCID 22902388, compound

HRID 1078351Notes

Reaction equation

HRID 1078351 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][N:10]([CH2:12][CH2:13][O:14][C:15]2[N:16]([CH3:27])[N:17]=[C:18]([C:20]3[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=3)[CH:19]=2)[CH3:11])=[CH:4][CH:3]=1.N1C=CC=CC=1.[C:34](OC(=O)C)(=[O:36])[CH3:35].Cl>ClCCl.C(O)(C)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][N:10]([CH2:12][CH2:13][O:14][C:15]2[N:16]([CH3:27])[N:17]=[C:18]([C:20]3[CH:21]=[CH:22][C:23]([O:26][C:34](=[O:36])[CH3:35])=[CH:24][CH:25]=3)[CH:19]=2)[CH3:11])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 7918Acetic AnhydrideHCID 135554909HCID 135554909, compound

Product 1

HCID 22902388HCID 22902388, compound

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 6344DichloromethaneSolvent

Procedure

100 mg of 3-{2-[N-(2-(4-chlorophenyl)-ethyl)-N-methylamino]-ethyloxy}-5-(4-hydroxyphenyl)-2-methylpyrazole (preparation see Example 9) were dissolved in 2 ml of dichloromethane. 0.15 ml of pyridine and 1 ml of acetic anhydride were added to the solution and the reaction mixture was stirred at room temperature for 24 hours. The reaction mixture was subsequently evaporated under reduced pressure, and the residue was taken up in aqueous sodium bicarbonate solution and extracted with dichloromethane. The organic phase was separated, dried and concentrated. The crude title compound which remained as a residue was taken up in tert-butyl methyl ether. To form a salt, a 2N solution of hydrochloric acid in isopropanol was added. The precipitated salt was separated. 80 mg of the hydrochloride of the title compound were obtained having a melting point of from 160° to 175° C.

Workup

  1. customThe reaction mixture was subsequently evaporated under reduced pressure
  2. extractionextracted with dichloromethane
  3. customThe organic phase was separated
  4. customdried
  5. concentrationconcentrated
  6. customTo form a salt
  7. customThe precipitated salt was separated

Sources & evidence

ORD record
ord-01bbc5c181e647128c8198db9b059c50
Source dataset
uspto-grants-1996_08
Patent number
US05547967

Reaction notes

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