Triethylamine → 2-[4-(2-[2-(2,2,2-Trifluoroethyl)guanidino]thiazol-4-yl)butylamino]benzimidazole

HRID 1902318Notes

Reaction equation

HRID 1902318 reaction equation
[F:1][C:2]([F:29])([F:28])[CH2:3][N:4]=[C:5]([NH2:27])[NH:6][C:7]1[S:8][CH:9]=[C:10]([CH2:12][CH2:13][CH2:14][CH2:15][NH:16][C:17]([NH:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[NH2:26])=S)[N:11]=1.C(N(CC)CC)C>CN(C)C=O.[N+]([O-])([O-])=O.[Ag+]>[F:1][C:2]([F:29])([F:28])[CH2:3][N:4]=[C:5]([NH2:27])[NH:6][C:7]1[S:8][CH:9]=[C:10]([CH2:12][CH2:13][CH2:14][CH2:15][NH:16][C:17]2[NH:26][C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=3[N:19]=2)[N:11]=1

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 212986982-[2-(2,2,2-Trifluoroethyl)-guanidino]-4-[4-(3-[2-aminophenyl]thioureido)butyl]thiazole

Product 1

HCID 212988022-[4-(2-[2-(2,2,2-Trifluoroethyl)guanidino]thiazol-4-yl)butylamino]benzimidazole

Reagents, catalysts & solvents 2

HCID 24470Silver NitrateCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-[2-(2,2,2-trifluoroethyl)-guanidino]-4-[4-(3-[2-aminophenyl]thioureido)butyl]thiazole (0.45 g.), silver nitrate (0.34 g.) and triethylamine (0.28 ml.) in dimethylformamide (3 ml.) was stirred vigorously at ambient temperature overnight. Hydrogen sulphide gas was then bubbled through the reaction mixture until no more solid precipitated. The reaction mixture was filtered through a pad of diatomaceous earth and the filtrate evaporated to dryness in vacuo. The residue was purified by low pressure liquid chromatography using chloroform/methanol/ammonia, 9:1:0.1 v/v/v as eluant to give 2-[4-(2-[2-(2,2,2-trifluoroethyl)guanidino]thiazol-4-yl)butylamino]benzimidazole which was converted to the hydrogen maleate salt (0.25 g.), mp. 183°-186°.

Workup

  1. customHydrogen sulphide gas was then bubbled through the reaction mixture until no more solid
  2. customprecipitated
  3. filtrationThe reaction mixture was filtered through a pad of diatomaceous earth
  4. customthe filtrate evaporated to dryness in vacuo
  5. customThe residue was purified by low pressure liquid chromatography

Sources & evidence

ORD record
ord-15a69dbcd22e425681a5952bf07e4499
Source dataset
uspto-grants-1982_12
Patent number
US04362728

Reaction notes

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