Methylhydrazine → 3-amino-1-methyl-5-[4-(2-[2-(2,2,2-trifluoroethyl)guanidino]thiazol-4-yl)butylamino]-1H-1,2,4-triazole dimaleate

HRID 34829Notes

Reaction equation

HRID 34829 reaction equation
[F:1][C:2]([F:25])([F:24])[CH2:3][N:4]=[C:5]([NH2:23])[NH:6][C:7]1[S:8][CH:9]=[C:10]([CH2:12][CH2:13][CH2:14][CH2:15][NH:16][C:17](=[N:20][C:21]#[N:22])SC)[N:11]=1.[CH3:26][NH:27][NH2:28].[C:29]([O-:36])(=[O:35])/[CH:30]=[CH:31]\[C:32]([O-:34])=[O:33]>CN(C)C=O.CC(C)=O>[C:29]([OH:36])(=[O:35])/[CH:30]=[CH:31]\[C:32]([OH:34])=[O:33].[C:29]([OH:36])(=[O:35])/[CH:30]=[CH:31]\[C:32]([OH:34])=[O:33].[NH2:22][C:21]1[N:20]=[C:17]([NH:16][CH2:15][CH2:14][CH2:13][CH2:12][C:10]2[N:11]=[C:7]([NH:6][C:5]([NH2:23])=[N:4][CH2:3][C:2]([F:25])([F:24])[F:1])[S:8][CH:9]=2)[N:27]([CH3:26])[N:28]=1

Participants

6

Reactant 3

HCID 6061MethylhydrazineHCID 5288227Maleate(2-)HCID 178503911HCID 178503911, compound

Product 1

HCID 1317128923-amino-1-methyl-5-[4-(2-[2-(2,2,2-trifluoroethyl)guanidino]thiazol-4-yl)butylamino]-1H-1,2,4-triazole dimaleate

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-[2-(2,2,2-trifluoroethyl)guanidino]-4-[4-(3-cyano-2-methylisothioureido)butyl]thiazole (0.23 g.) and N-methylhydrazine (0.6 g.) in dimethylformamide (15 ml.) was heated at 40°-45° for 40 hours. The solvent was removed and the residue applied to 2 t.l.c. plates which were developed with chloroform/methanol/ammonia 9:1:0.1 v/v/v. The oil obtained was converted to a maleate in acetone to give 3-amino-1-methyl-5-[4-(2-[2-(2,2,2-trifluoroethyl)guanidino]thiazol-4-yl)butylamino]-1H-1,2,4-triazole dimaleate (56.8 mg.), m.p. 181°-183°.

Workup

  1. temperaturewas heated at 40°-45° for 40 hours
  2. customThe solvent was removed
  3. customThe oil obtained

Sources & evidence

ORD record
ord-5da0699cd8394959bd08d967eef560da
Source dataset
uspto-grants-1988_08
Patent number
US04762932

Reaction notes

Loading…