5-(3-Amino-1H-pyrazol-1-yl)pentanamide → 3-((Imino((2,2,2-trifluoroethyl)amino)methyl)amino)1H-pyrazole-1-pentamide

HRID 543793Notes

Reaction equation

HRID 543793 reaction equation
[NH2:1][C:2]1[CH:6]=[CH:5][N:4]([CH2:7][CH2:8][CH2:9][CH2:10][C:11]([NH2:13])=[O:12])[N:3]=1.I.[F:15][C:16]([F:24])([F:23])[CH2:17][NH:18][C:19](=[NH:22])SC.C(Cl)(Cl)Cl.CO.N>>[F:15][C:16]([F:24])([F:23])[CH2:17][N:18]=[C:19]([NH2:22])[NH:1][C:2]1[CH:6]=[CH:5][N:4]([CH2:7][CH2:8][CH2:9][CH2:10][C:11]([NH2:13])=[O:12])[N:3]=1

Participants

4

Reactant 3

HCID 202027755-(3-Amino-1H-pyrazol-1-yl)pentanamideHCID 21866414Chloroform methanol ammoniaHCID 178504040HCID 178504040, compound

Product 1

HCID 1347783-((Imino((2,2,2-trifluoroethyl)amino)methyl)amino)1H-pyrazole-1-pentamide

Procedure

A mixture of 5-(3-aminopyrazol-1-yl]valeramide (18.2 mg.) and (2,2,2-trifluoroethyl)-S-methylisothiourea hydroiodide (51 mg.) was heated at 100° for 20 minutes. Preparative high pressure liquid chromatography on silica gel, using CHCl3 /MeOH/ammonia (s.g. 0.880) 8:2:0.5 v/v/v as eluant gave 5-[3-(2-[2,2,2-trifluoroethyl]guanidino)pyrazol-1-yl]valeramide, m.p. 129°-130° (40%).

Workup

  1. temperaturewas heated at 100° for 20 minutes

Sources & evidence

ORD record
ord-009ef290223244d8848b37b9cb02da69
Source dataset
uspto-grants-1984_05
Patent number
US04447441

Reaction notes

Loading…