Dimethylformamide → HCID 178485208, compound

HRID 34782

Reaction equation

HRID 34782 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[N:5]=[C:4]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][NH:14][C:15]([NH:21][CH3:22])=[N:16][S:17]([CH3:20])(=[O:19])=[O:18])[N:3]=1.[F:23][C:24]([F:30])([F:29])[CH2:25][N:26]=[C:27]=S.C[N:32](C)C=O>>[NH2:8][C:6]1[N:7]=[C:2]([NH:1][C:27]([NH2:32])=[N:26][CH2:25][C:24]([F:30])([F:29])[F:23])[N:3]=[C:4]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][NH:14][C:15]([NH:21][CH3:22])=[N:16][S:17]([CH3:20])(=[O:19])=[O:18])[N:5]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 138837771,1,1-Trifluoro-2-isothiocyanatoethaneHCID 178485209HCID 178485209, compound

Product 1

HCID 178485208HCID 178485208, compound

Procedure

A mixture of 2,4-diamino-6-[5-(2-methanesulphonyl-3-methylguanidino)pentyl]-1,3,5-triazine (0.4 g.), 2,2,2-trifluoroethylisothiocyanate (0.4 g.) and dimethylformamide (0.5 ml.) was heated at 120° for 1 hour and then at 60° for 18 hours. The mixture was evaporated to dryness, the residue partitioned between water and ethyl acetate, and the ethyl phase was separated, dried, and evaporated to dryness. The residue was dissolved in saturated ethanolic ammonia (10 ml.) and the solution treated with yellow mercuric oxide (0.5 g.). The mixture was stirred at room temperature for 18 hours, filtered and the filtrate evaporated to dryness. The residue was purified by chromatography using ethyl acetate/methanol/ammonia 6:1:0.5 v/v/v as developing solvent to give 2-amino-4-[2-(2,2,2-trifluoroethyl)guanidino]-6-[5-(2-methanesulphonyl-3-methylguanidino)pentyl]-1,3,5-triazine (0.07 g.) characterised as the bishydrogen maleate, m.p. 131°-133° after recrystallisation from acetone.

Workup

  1. temperaturewas heated at 120° for 1 hour
  2. customThe mixture was evaporated to dryness
  3. customthe residue partitioned between water and ethyl acetate
  4. customthe ethyl phase was separated
  5. customdried
  6. customevaporated to dryness
  7. dissolutionThe residue was dissolved in saturated ethanolic ammonia (10 ml.)
  8. additionthe solution treated with yellow mercuric oxide (0.5 g.)
  9. filtrationfiltered
  10. customthe filtrate evaporated to dryness
  11. customThe residue was purified by chromatography

Sources & evidence

ORD record
ord-abff89b40d01492fadfc24f49225218e
Source dataset
uspto-grants-1988_08
Patent number
US04762932

Linked notes

Loading…