4-(5-Aminomethylfuran-2-yl)-2-(diaminomethyleneamino)thiazole → HCID 178502527, compound

HRID 1033070Notes

Reaction equation

HRID 1033070 reaction equation
[NH2:1][CH2:2][C:3]1[O:7][C:6]([C:8]2[N:9]=[C:10]([N:13]=[C:14]([NH2:16])[NH2:15])[S:11][CH:12]=2)=[CH:5][CH:4]=1.[CH3:17][O:18][C:19](=[O:25])[NH:20][C:21](=[NH:24])SC>C(N(CC)CC)C>[NH2:15][C:14](=[N:13][C:10]1[S:11][CH:12]=[C:8]([C:6]2[O:7][C:3]([CH2:2][NH:1][C:21]([NH2:24])=[N:20][C:19]([O:18][CH3:17])=[O:25])=[CH:4][CH:5]=2)[N:9]=1)[NH2:16]

Participants

4

Reactant 2

HCID 103992684-(5-Aminomethylfuran-2-yl)-2-(diaminomethyleneamino)thiazoleHCID 145796808N-carbomethoxy-S-methylisothiourea2×

Product 1

HCID 178502527HCID 178502527, compoundYield 23.3%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A suspension of 4-(5-aminomethylfuran-2-yl)-2-(diaminomethyleneamino)thiazole (1.6 g), imino(methylthio)methylcarbamic acid methylester (1.2 g) and triethylamine (1.5 g) was stirred at room temperature for 26 hours and then refluxed for 2.5 hours. Imino(methylthio)methylcarbamic acid methylester (1.0 g) was added to the reaction mixture and the mixture was refluxed for 10 hours. The solvent was removed under reduced pressure. The residue was chromatographed on a silica gel column eluting with a mixture of chloroform and methanol (10:1, V/V). Recrystallization from a mixture of methanol and diisopropyl ether afforded 2-(diaminomethyleneamino)-4-[5-(2-methoxycarbonylguanidino)methylfuran-2-yl]thiazole (530 mg).

Workup

  1. temperaturerefluxed for 2.5 hours
  2. temperaturethe mixture was refluxed for 10 hours
  3. customThe solvent was removed under reduced pressure
  4. customThe residue was chromatographed on a silica gel column
  5. washeluting with a mixture of chloroform and methanol (10:1, V/V)
  6. customRecrystallization
  7. additionfrom a mixture of methanol and diisopropyl ether

Sources & evidence

ORD record
ord-f94d2961fa624e60b7d8962b9d02f9d9
Source dataset
uspto-grants-1994_05
Patent number
US05308857

Reaction notes

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