6-Bromonicotinic acid → (6-Bromopyridin-3-yl)[4-(3,5,6-trimethylpyridin-2-yl)piperazin-1-yl]methanone

HRID 1804098Notes

Reaction equation

HRID 1804098 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][N:3]=1.[CH3:11][C:12]1[C:13]([N:20]2[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]2)=[N:14][C:15]([CH3:19])=[C:16]([CH3:18])[CH:17]=1>>[Br:1][C:2]1[N:3]=[CH:4][C:5]([C:6]([N:23]2[CH2:24][CH2:25][N:20]([C:13]3[C:12]([CH3:11])=[CH:17][C:16]([CH3:18])=[C:15]([CH3:19])[N:14]=3)[CH2:21][CH2:22]2)=[O:8])=[CH:9][CH:10]=1

Participants

3

Reactant 2

HCID 2389326-Bromonicotinic acidHCID 584848231-(3,5,6-Trimethylpyridin-2-yl)piperazine

Product 1

HCID 58484612(6-Bromopyridin-3-yl)[4-(3,5,6-trimethylpyridin-2-yl)piperazin-1-yl]methanoneYield 79%

Procedure

To 1-(3,5,6-trimethylpyridin-2-yl)piperazine hydrochloride described in Preparation Example 52 were added ethyl acetate and 1N aqueous sodium hydroxide solution, and the mixture was extracted with ethyl acetate and washed with saturated brine. The solvent was evaporated to give 1-(3,5,6-trimethylpyridin-2-yl)piperazine (470 mg). By reaction and treatment in the same manner as in Preparation Example 27 and using 6-bromonicotinic acid (407 mg) and 1-(3,5,6-trimethylpyridin-2-yl)piperazine (470 mg), the title compound (620 mg) was obtained.

Workup

  1. customBy reaction and treatment in the same manner
  2. customas in Preparation Example 27

Sources & evidence

ORD record
ord-a5833541b78c47cbbb8357bcfae75358
Source dataset
uspto-grants-2013_01
Patent number
US08354401B2

Reaction notes

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