3-Amino-4-methoxy-1,2,5-thiadiazole 1-oxide → HCID 178512517, compound

HRID 1980744Notes

Reaction equation

HRID 1980744 reaction equation
[NH:1]([C:5]1[CH:6]=[C:7]([CH:13]=[CH:14][CH:15]=1)[O:8][CH2:9][CH2:10][CH2:11][NH2:12])[C:2]([NH2:4])=[NH:3].[NH2:16][C:17]1[C:21](OC)=[N:20][S:19](=[O:24])[N:18]=1>CO>[NH2:16][C:17]1[C:21]([NH:12][CH2:11][CH2:10][CH2:9][O:8][C:7]2[CH:13]=[CH:14][CH:15]=[C:5]([NH:1][C:2]([NH2:4])=[NH:3])[CH:6]=2)=[N:20][S:19](=[O:24])[N:18]=1

Participants

4

Reactant 2

HCID 159612163-Amino-4-methoxy-1,2,5-thiadiazole 1-oxideHCID 178512516HCID 178512516, compound

Product 1

HCID 178512517HCID 178512517, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of crude 3-(3-guanidinophenoxy)propylamine [prepared in Step D] in 10 ml of methanol was added 3-amino-4-methoxy-1,2,5-thiadiazole 1-oxide (0.59 g; 4.0 mmoles) and the mixture was stirred at ambient temperature for 17 hours and then heated at 50° for 2.5 hours. The reaction mixture was filtered, evaporated under reduced pressure and the residue was chromatographed by flash chromatography on 75 g of silica gel (230-400 mesh) using methanol-methylene chloride. The appropriate fractions were combined and evaporated under reduced pressure to yield 0.25 g of the title compound as an oil; TLC [silica gel/CH2Cl2 :CH3OH (4:1)] gave Rf=0.21.

Workup

  1. temperatureheated at 50° for 2.5 hours
  2. filtrationThe reaction mixture was filtered
  3. customevaporated under reduced pressure
  4. customthe residue was chromatographed by flash chromatography on 75 g of silica gel (230-400 mesh)
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-c7dc44291893444894e167e882f6e3cc
Source dataset
uspto-grants-1985_04
Patent number
US04510309

Reaction notes

Loading…