Triethylamine → HCID 178434609, compound

HRID 1253170Notes

Reaction equation

HRID 1253170 reaction equation
Cl.[NH:2]([C:6]1[CH:10]=[N:9][N:8]([CH2:11][CH2:12][CH2:13][CH2:14][C:15](=[NH:18])OC)[N:7]=1)[C:3]([NH2:5])=[NH:4].C(N(CC)CC)C.[C:26]([NH:29][NH2:30])(=O)[CH3:27].[C:31]([O-:38])(=[O:37])/[CH:32]=[CH:33]/[C:34]([O-:36])=[O:35]>CO>[C:31]([OH:38])(=[O:37])/[CH:32]=[CH:33]/[C:34]([OH:36])=[O:35].[CH3:27][C:26]1[N:18]=[C:15]([CH2:14][CH2:13][CH2:12][CH2:11][N:8]2[N:7]=[C:6]([NH:2][C:3]([NH2:5])=[NH:4])[CH:10]=[N:9]2)[NH:30][N:29]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 14039AcetohydrazideHCID 5460307FumarateHCID 178496791HCID 178496791, compound

Product 1

HCID 178434609HCID 178434609, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Crude methyl 5-(4-guanidino-1,2,3-triazol-2-yl)valerimidate hydrochloride (0.42 g.) in MeOH (8 ml.) was treated with triethylamine (0.35 g.) followed after 0.5 hours by acethydrazide (0.13 g.). After a further 0.5 hours the solution was heated under reflux for 6 hours then evaporated to dryness. The residue was purified by medium pressure chromatography using chloroform/MeOH/aqueous ammonia (s.g. 0.880) 8:2:0.1 v/v/v as eluant to give a gum which was converted to the fumarate in MeOH. The solid was filtered and washed with warm MeOH to give 3-methyl-5-[4-(4-guanidino-1,2,3-triazol-2-yl)butyl]-1,2,4-triazole fumarate (yield 19%) having the following n.m.r. in d6DMSO:- 1.4-2.1 (m, 4H); 2.15 (s, 3H); 2.61 (t, 2H); 4.4 (t, 2H); 6.68 (s, 1H); 7.08 (s, 1H); 7.26 (br s, 4H).

Workup

  1. temperatureAfter a further 0.5 hours the solution was heated
  2. temperatureunder reflux for 6 hours
  3. customthen evaporated to dryness
  4. customThe residue was purified by medium pressure chromatography
  5. customto give a gum which
  6. filtrationThe solid was filtered
  7. washwashed with warm MeOH

Sources & evidence

ORD record
ord-dd34751dc57d4910befcb6e985998eea
Source dataset
uspto-grants-1988_05
Patent number
US04748165

Reaction notes

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