HCID 14625097, compound → 3-Amino-4-{2-[(5-piperidinomethyl-2-furyl)methylthio]ethylamino}-1,2,5-thiadiazole 1-oxide

HRID 1075124Notes

Reaction equation

HRID 1075124 reaction equation
[N:1]1([CH2:7][C:8]2[O:12][C:11]([CH2:13][S:14][CH2:15][CH2:16][NH2:17])=[CH:10][CH:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[NH2:18][C:19]1[C:23](OC)=[N:22][S:21](=[O:26])[N:20]=1>CO>[NH2:18][C:19]1[C:23]([NH:17][CH2:16][CH2:15][S:14][CH2:13][C:11]2[O:12][C:8]([CH2:7][N:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)=[CH:9][CH:10]=2)=[N:22][S:21](=[O:26])[N:20]=1

Participants

4

Reactant 2

HCID 14625097HCID 14625097, compoundHCID 159612163-Amino-4-methoxy-1,2,5-thiadiazole 1-oxide

Product 1

HCID 159612153-Amino-4-{2-[(5-piperidinomethyl-2-furyl)methylthio]ethylamino}-1,2,5-thiadiazole 1-oxideYield 64%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of 2-[(5-piperidinomethyl-2-furyl)methylthio]ethylamine (4.0 g; 15.7 mmoles) [prepared according to the procedure described in Belgian Pat. No. 857,388 (U.S. Pat. No. 4,128,658)] in 25 ml of methanol was added all at once to a stirred suspension of 3-amino-4-methoxy-1,2,5-thiadiazole 1-oxide (2.31 g; 15.7 mmoles) [prepared in Step A] in 25 ml of methanol at ambient temperature. After stirring for 16 hours, the solution was evaporated under reduced pressure and the residue chromatographed by flash chromatography on 100 g of silica gel (230-400 mesh) using methanol-acetonitrile. The appropriate fractions were combined and evaporated to give 3.71 g of product. Recrystallization from 95% aqueous ethanol with charcoal treatment yielded the title compound, mp 161°-163°.

Workup

  1. customthe solution was evaporated under reduced pressure
  2. customthe residue chromatographed by flash chromatography on 100 g of silica gel (230-400 mesh)
  3. customevaporated

Sources & evidence

ORD record
ord-c03c3355578e44cd9219ebb4e18ed0a5
Source dataset
uspto-grants-1983_07
Patent number
US04394508

Reaction notes

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