3-({4-[(Piperidin-1-yl)methyl]pyridin-2-yl}oxy)propan-1-amine → 3-Amino-4-[3-(4-piperidinomethyl-2-pyridyloxy)propylamino]-1,2,5-thiadiazole 1-oxide

HRID 325512Notes

Reaction equation

HRID 325512 reaction equation
[N:1]1([CH2:7][C:8]2[CH:13]=[CH:12][N:11]=[C:10]([O:14][CH2:15][CH2:16][CH2:17][NH2:18])[CH:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[NH2:19][C:20]1[C:24](OC)=[N:23][S:22](=[O:27])[N:21]=1>CO>[NH2:19][C:20]1[C:24]([NH:18][CH2:17][CH2:16][CH2:15][O:14][C:10]2[CH:9]=[C:8]([CH2:7][N:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)[CH:13]=[CH:12][N:11]=2)=[N:23][S:22](=[O:27])[N:21]=1

Participants

4

Reactant 2

HCID 146251023-({4-[(Piperidin-1-yl)methyl]pyridin-2-yl}oxy)propan-1-amineHCID 159612163-Amino-4-methoxy-1,2,5-thiadiazole 1-oxide

Product 1

HCID 159613413-Amino-4-[3-(4-piperidinomethyl-2-pyridyloxy)propylamino]-1,2,5-thiadiazole 1-oxideYield 66.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of the product of Step A (6.5 g; 26.0 mmoles) in 90 ml of methanol was reacted with 3-amino-4-methoxy-1,2,5-thiadiazole 1-oxide (3.84 g; 26.0 mmoles) according to the general procedures described in U.S. Pat. No. 4,374,248 to give 6.33 g of product. Recrystallization from methanolacetonitrile yielded the title compound, mp 154°-158° C.

Sources & evidence

ORD record
ord-5f36d9bc7ccd4108947756579e4dc383
Source dataset
uspto-grants-1984_04
Patent number
US04440933

Reaction notes

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