Triethylamine → 2-(Diaminomethyleneamino)-4-[6-(3-methylureido)methylpyridin-2-yl]thiazole

HRID 1491858Notes

Reaction equation

HRID 1491858 reaction equation
[CH3:1][N:2]=[C:3]=[O:4].Cl.Cl.Cl.[NH2:8][CH2:9][C:10]1[N:15]=[C:14]([C:16]2[N:17]=[C:18]([N:21]=[C:22]([NH2:24])[NH2:23])[S:19][CH:20]=2)[CH:13]=[CH:12][CH:11]=1.C(N(CC)CC)C.C(=O)([O-])[O-].[K+].[K+]>O.C(OCC)(=O)C.CO.O1CCCC1>[NH2:23][C:22](=[N:21][C:18]1[S:19][CH:20]=[C:16]([C:14]2[CH:13]=[CH:12][CH:11]=[C:10]([CH2:9][NH:8][C:3]([NH:2][CH3:1])=[O:4])[N:15]=2)[N:17]=1)[NH2:24]

Participants

9

Reactant 4

HCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 12228Methyl IsocyanateHCID 189538374-(6-Aminomethylpyridin-2-yl)-2-(diaminomethyleneamino)thiazole trihydrochloride

Product 1

HCID 104703552-(Diaminomethyleneamino)-4-[6-(3-methylureido)methylpyridin-2-yl]thiazole

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Methyl isocyanate (0.24 ml) was added to a mixture of 4-(6-aminomethylpyridin-2-yl)-2-(diaminomethyleneamino)thiazole trihydrochloride (1.2 g) and triethylamine (1.4 ml) in a solution of tetrahydrofuran (18 ml) and methanol (6 ml) and the mixture was stirred at ambient temperature for 1 hour. To the mixture was added a mixture of ethyl acetate and water, and the mixture was adjusted to pH 9.5 with 20% aqueous potassium carbonate. The separated organic layer was dried over magnesium sulfate and evaporated to give 2-(diaminomethyleneamino)-4-[6-(3-methylureido)methylpyridin-2-yl]thiazole (0.92 g).

Workup

  1. additionTo the mixture was added
  2. dry with materialThe separated organic layer was dried over magnesium sulfate
  3. customevaporated

Sources & evidence

ORD record
ord-1736708c777e493ab29a162bfdb198a9
Source dataset
uspto-grants-1994_12
Patent number
US05371097

Reaction notes

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