3-(4-Piperidinomethylpyrazol-1-yloxy)propylamine → 4-Methylamino-3-[3-(4-piperidinomethylpyrazol-1-yloxy)propylamino]-1,2,5-thiadiazole 1-oxide

HRID 232025Notes

Reaction equation

HRID 232025 reaction equation
[CH3:1][NH:2][C:3]1[C:4](OC)=[N:5][S:6](=[O:8])[N:7]=1.[N:11]1([CH2:17][C:18]2[CH:19]=[N:20][N:21]([O:23][CH2:24][CH2:25][CH2:26][NH2:27])[CH:22]=2)[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1>CO>[CH3:1][NH:2][C:3]1[C:4]([NH:27][CH2:26][CH2:25][CH2:24][O:23][N:21]2[CH:22]=[C:18]([CH2:17][N:11]3[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]3)[CH:19]=[N:20]2)=[N:5][S:6](=[O:8])[N:7]=1

Participants

4

Reactant 2

HCID 138232143-(4-Piperidinomethylpyrazol-1-yloxy)propylamineHCID 200307843-Methoxy-4-methylamino-1,2,5-thiadiazole 1-oxide

Product 1

HCID 159618904-Methylamino-3-[3-(4-piperidinomethylpyrazol-1-yloxy)propylamino]-1,2,5-thiadiazole 1-oxideYield 74.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2.4 g of 4-methylamino-3-methoxy-1,2,5-thiadiazole 1-oxide and 3.5 g of 3-(4-piperidinomethylpyrazol-1-yloxy)propylamine are dissolved in 50 ml of methanol, and the solution is left to stand at room temperature for 12 hours. The solution is then evaporated down and the residue is chromatographed over neutral Al2O3 (activity level III), using methylene chloride/3% strength methanol as the mobile phase. 4 g of the title compound are obtained, the product being crystallized from ethyl acetate.

Workup

  1. waitthe solution is left
  2. customThe solution is then evaporated down
  3. customthe residue is chromatographed over neutral Al2O3 (activity level III)

Sources & evidence

ORD record
ord-48c9ad669529453197a5fc909ac47d69
Source dataset
uspto-grants-1989_07
Patent number
US04851410

Reaction notes

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