Sodium Hydroxide → 1-Methyl-3-amino-5-[3-(4-piperidinomethylpyrazol-1-yloxy)propylamino]-1,2,4-triazole

HRID 232023Notes

Reaction equation

[N:1]1([CH2:7][C:8]2[CH:9]=[N:10][N:11]([O:13][CH2:14][CH2:15][CH2:16][NH2:17])[CH:12]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:18]([N:20]=[C:21]([N:24]([CH3:33])[N:25]=CC1C=CC=CC=1)SC)#[N:19].[OH-].[Na+]>Cl>[CH3:33][N:24]1[C:21]([NH:17][CH2:16][CH2:15][CH2:14][O:13][N:11]2[CH:12]=[C:8]([CH2:7][N:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)[CH:9]=[N:10]2)=[N:20][C:18]([NH2:19])=[N:25]1

Participants

Conditions

Temperature: 70 °C

Procedure

5 g of 3-(4-piperidinomethylpyrazol-1-yloxy)-propylamine and 4.9 g of methyl N-cyano-1-methyl-2-(phenylmethylene)-hydrazinecarboximidothioate are combined, and heated at 70° C. for 1 hour. Thereafter, the reaction mixture is taken up with 40 ml of 1N hydrochloric acid, stirred for 1 hour at room temperature, rendered alkaline with sodium hydroxide solution and extracted with methylene chloride. The residue which remains after the solvent has been expelled is chromatographed over neutral Al2O3 (activity level III), using methylene chloride/3% strength methanol as the mobile phase. The oily title compound is reacted with tartaric acid in isopropanol to give an amorphous solid.

Workup

extractionextracted with methylene chloride
customhas been expelled is chromatographed over neutral Al2O3 (activity level III)
customThe oily title compound is reacted with tartaric acid in isopropanol
customto give an amorphous solid

Sources & evidence

ORD record: ord-138c7c0278b04dafbb97a21f50060891
Source dataset: uspto-grants-1989_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04851410

Reaction notes

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