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

HRID 364316Notes

Reaction equation

HRID 364316 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.), m.p. 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-74bd9078cd5948118f1b262479355627
Source dataset
uspto-grants-1986_08
Patent number
US04604465

Reaction notes

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