Formic Acid → 3-{3-[N-(2-(3,4-Dimethoxyphenyl)-ethyl)-N-methylamino]-propyloxy}-5-(3,4-dimethoxyphenyl)-pyrazole

HRID 1078355Notes

Reaction equation

HRID 1078355 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][N:13]([CH2:15][CH2:16][CH2:17][O:18][C:19]2[N:20](CC3C=CC=CC=3)[N:21]=[C:22]([C:24]3[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[C:26]([O:32][CH3:33])[CH:25]=3)[CH:23]=2)[CH3:14])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].C(O)=O>CO.[Pd]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][N:13]([CH2:15][CH2:16][CH2:17][O:18][C:19]2[CH:23]=[C:22]([C:24]3[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[C:26]([O:32][CH3:33])[CH:25]=3)[NH:21][N:20]=2)[CH3:14])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

5

Reactant 2

HCID 284Formic AcidHCID 229023713-{3-[N-(2-(3,4-Dimethoxyphenyl)-ethyl)-N-methylamino]-propyloxy}-5-(3,4-dimethoxyphenyl)-2-benzyl-pyrazole

Product 1

HCID 152835203-{3-[N-(2-(3,4-Dimethoxyphenyl)-ethyl)-N-methylamino]-propyloxy}-5-(3,4-dimethoxyphenyl)-pyrazoleYield 95.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

2 g of 3-{3-[N-(2-(3,4-Dimethoxyphenyl)-ethyl)-N-methylamino]-propyloxy}-5-(3,4-dimethoxyphenyl)-2-benzylpyrazole prepared according to Example 13 were dissolved in 10 ml of methanol and added to 2 g of palladium black under nitrogen. 5.5 ml of 98% strength formic acid were added to the solution, which was stirred under nitrogen. After the mixture had been stirred for 3 hours under nitrogen the catalyst was filtered out, and the filtrate was concentrated by evaporation. The oily residue was taken up in saturated sodium carbonate solution and extracted repeatedly with ethyl acetate. The combined organic phases were dried with sodium sulfate and concentrated by evaporation. 1.6 g of 3-{3-[N-(2-(3,4-Dimethoxyphenyl)-ethyl)-N-methylamino]-propyloxy}-5-(3,4-dimethoxyphenyl)-pyrazole were obtained as an oily base. This base was converted analogously to Example 1 E) into the hydrochloride having a melting point of 189° to 192° C.

Workup

  1. stirringAfter the mixture had been stirred for 3 hours under nitrogen the catalyst
  2. filtrationwas filtered out
  3. concentrationthe filtrate was concentrated by evaporation
  4. extractionextracted repeatedly with ethyl acetate
  5. dry with materialThe combined organic phases were dried with sodium sulfate
  6. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-c0ec37052a51466d9709c3253b040448
Source dataset
uspto-grants-1996_08
Patent number
US05547967

Reaction notes

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