Triethylamine → 4-[6-(1-Amino-3,4-dioxo-1-cyclobuten-2-yl)aminomethylpyridin-2-yl]-2-(diaminomethyleneamino)thiazole hydrochloride

HRID 1491862Notes

Reaction equation

HRID 1491862 reaction equation
[ClH:1].Cl.Cl.[NH2:4][CH2:5][C:6]1[N:11]=[C:10]([C:12]2[N:13]=[C:14]([N:17]=[C:18]([NH2:20])[NH2:19])[S:15][CH:16]=2)[CH:9]=[CH:8][CH:7]=1.C(N(CC)CC)C.[NH2:28][C:29]1[C:32](=[O:33])[C:31](=[O:34])[C:30]=1OCC>CO>[ClH:1].[NH2:28][C:29]1[C:32](=[O:33])[C:31](=[O:34])[C:30]=1[NH:4][CH2:5][C:6]1[N:11]=[C:10]([C:12]2[N:13]=[C:14]([N:17]=[C:18]([NH2:20])[NH2:19])[S:15][CH:16]=2)[CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 151463363-Amino-4-ethoxycyclobut-3-ene-1,2-dioneHCID 189538374-(6-Aminomethylpyridin-2-yl)-2-(diaminomethyleneamino)thiazole trihydrochloride

Product 1

HCID 189538944-[6-(1-Amino-3,4-dioxo-1-cyclobuten-2-yl)aminomethylpyridin-2-yl]-2-(diaminomethyleneamino)thiazole hydrochlorideYield 73.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 4-(6-aminomethylpyridin-2-yl)-2-(diaminomethyleneamino)thiazole trihydrochloride (1.5 g), triethylamine (1.8 ml) and 1-amino-2-ethoxy-1-cyclobutene-3,4-dione (0.65 g) in methanol (30 ml) was heated under reflux for 7 hours. The solvent was removed by concentration in vacuo. To the residue was added a mixture of water and ethyl acetate, and the mixture was adjusted to pH 1.0 with 6N-hydrochloric acid. The isolated precipitate was collected by filtration and dried. The precipitate was recrystallized from an aqueous N,N-dimethylformamide to give 4-[6-(1-amino-3,4-dioxo-1-cyclobuten-2-yl)aminomethylpyridin-2-yl]-2-(diaminomethyleneamino)thiazole hydrochloride (1.17 g).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 7 hours
  3. customThe solvent was removed by concentration in vacuo
  4. additionTo the residue was added
  5. additiona mixture of water and ethyl acetate
  6. filtrationThe isolated precipitate was collected by filtration
  7. customdried
  8. customThe precipitate was recrystallized from an aqueous N,N-dimethylformamide

Sources & evidence

ORD record
ord-f6824f9f12ef4d0db0995a9b7652a932
Source dataset
uspto-grants-1994_12
Patent number
US05371097

Reaction notes

Loading…