3,4-Dimethoxy-1,2,5-thiadiazole 1-oxide → 3-[4-(3-Amino-5-bromopyrid-2-yl)butylamino]-4-methoxy-1,2,5-thiadiazole-1-oxide

HRID 371406Notes

Reaction equation

HRID 371406 reaction equation
[CH3:1][O:2][C:3]1[C:7](OC)=[N:6][S:5](=[O:10])[N:4]=1.[NH2:11][C:12]1[C:13]([CH2:19][CH2:20][CH2:21][CH2:22][NH2:23])=[N:14][CH:15]=[C:16]([Br:18])[CH:17]=1>CO>[NH2:11][C:12]1[C:13]([CH2:19][CH2:20][CH2:21][CH2:22][NH:23][C:7]2[C:3]([O:2][CH3:1])=[N:4][S:5](=[O:10])[N:6]=2)=[N:14][CH:15]=[C:16]([Br:18])[CH:17]=1

Participants

4

Reactant 2

HCID 129139473,4-Dimethoxy-1,2,5-thiadiazole 1-oxideHCID 145374593-Amino-5-bromo-(4-aminobutyl)pyridine

Product 1

HCID 159623603-[4-(3-Amino-5-bromopyrid-2-yl)butylamino]-4-methoxy-1,2,5-thiadiazole-1-oxideYield 74%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of 3,4-dimethoxy-1,2,5-thiadiazole-1-oxide (0.995 g) in methanol (25 ml) was reacted with a solution of 3-amino-5-bromo-(4-aminobutyl)pyridine (1.5 g) in methanol (25 ml) at room temperature for 3 hours. The solvent was removed in vacuo and the residue was chromatographed on silica in ethanol to give an oil which was triturated with ether and recrystallised from ethanol/ether to give 3-[4-(3-amino-5-bromopyrid-2-yl)butylamino]-4-methoxy-1,2,5-thiadiazole-1-oxide (1.7 g) m.p. 118°-120° C.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was chromatographed on silica in ethanol
  3. customto give an oil which
  4. customwas triturated with ether
  5. customrecrystallised from ethanol/ether

Sources & evidence

ORD record
ord-b242893aab1c434bad0799f465662436
Source dataset
uspto-grants-1985_07
Patent number
US04532252

Reaction notes

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