Ammonia → Ether 3-[4-(3-amino-5-bromopyrid-2-yl)butylamino]-4-amino-1,2,5-thiadiazole-1-oxide

HRID 1607064Notes

Reaction equation

HRID 1607064 reaction equation
CO[C:3]1[C:7]([O:8][CH3:9])=NS(=O)[N:4]=1.N[C:12]1C(CCCCN)=NC=C(Br)C=1.[NH2:24][C:25]1[C:26]([CH2:32][CH2:33][CH2:34][CH2:35][NH:36][C:37]2[C:41](OC)=[N:40][S:39](=[O:44])[N:38]=2)=[N:27][CH:28]=[C:29]([Br:31])[CH:30]=1.NC1C(C2(OC)NS(=O)N=C2)=NC=C(Br)C=1.N>CO.C(Cl)(Cl)Cl>[CH3:3][CH2:7][O:8][CH2:9][CH3:12].[NH2:24][C:25]1[C:26]([CH2:32][CH2:33][CH2:34][CH2:35][NH:36][C:37]2[C:41]([NH2:4])=[N:40][S:39](=[O:44])[N:38]=2)=[N:27][CH:28]=[C:29]([Br:31])[CH:30]=1

Participants

8

Reactant 5

HCID 222AmmoniaHCID 129139473,4-Dimethoxy-1,2,5-thiadiazole 1-oxideHCID 145374593-Amino-5-bromo-(4-aminobutyl)pyridineHCID 159623603-[4-(3-Amino-5-bromopyrid-2-yl)butylamino]-4-methoxy-1,2,5-thiadiazole-1-oxideHCID 867433534-(3-Amino-5-bromopyrid-2-yl)-4-methoxy-1,2,5-thiadiazole-1-oxide

Product 1

HCID 86740210Ether 3-[4-(3-amino-5-bromopyrid-2-yl)butylamino]-4-amino-1,2,5-thiadiazole-1-oxideYield 9.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 6212ChloroformSolvent

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. (g) Reaction of 3-[4-(3-amino-5-bromopyrid-2-yl)-4-methoxy-1,2,5-thiadiazole-1-oxide (0.56 g) with methanolic ammonia solution (50 ml) at room temperature overnight gave after chromatography on silica in chloroform and trituration with ether 3-[4-(3-amino-5-bromopyrid-2-yl)butylamino]-4-amino-1,2,5-thiadiazole-1-oxide (0.19 g) m.p. 105°-109° 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
  6. customto give

Sources & evidence

ORD record
ord-357272ff030e41c1ab1609e5f6bd04f6
Source dataset
uspto-grants-1989_09
Patent number
US04863936

Reaction notes

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