Triethylamine → HCID 178485206, compound
Reaction equation
Cl.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.[CH2:21]([N:23]([CH2:26]C)CC)C.[CH3:28][S:29]([N:32]=C(SC)SC)(=[O:31])=[O:30]>C(O)C>[NH2:19][C:18](=[N:17][C:14]1[S:15][CH:16]=[C:12]([C:10]2[CH:9]=[CH:8][CH:7]=[C:6]([CH2:5][NH:4][C:21]([NH:23][CH3:26])=[N:32][S:29]([CH3:28])(=[O:31])=[O:30])[N:11]=2)[N:13]=1)[NH2:20]Participants
5
Procedure
A mixture of 4-(6-aminomethylpyridin-2-yl)-2-(diaminomethyleneamino)thiazole trihydrochloride (1.5 g), triethylamine (1.8 ml) and dimethyl N-methanesulfonyldithiocarbonimidate (0.8 g) in ethanol (30 ml) was heated under reflux for 5 hours. The solvent was removed by concentration in vacuo. To the residue was added to a mixture of 40% aqueous methylamine (4.0 ml) in N,N-dimethylformamide (13 ml) and the mixture was stirred at ambient temperature for 30 hours. The reaction mixture was added a water and the isolated precipitate was collected by filtration to give 2-(diaminomethyleneamino)-4-[6-(2-methanesulfonyl-3-methylguanidino)methylpyridin-2-yl]thiazole (1.12 g).
Workup
- temperaturewas heated
- temperatureunder reflux for 5 hours
- customThe solvent was removed by concentration in vacuo
- additionTo the residue was added to a mixture of 40% aqueous methylamine (4.0 ml) in N,N-dimethylformamide (13 ml)
- additionThe reaction mixture was added a water
- filtrationthe isolated precipitate was collected by filtration
Sources & evidence
- ORD record
- ord-461247dde3d042289adb42e5382bacb8
- Source dataset
- uspto-grants-1994_11
- Patent number
- US05364871
Reaction notes
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